Science of Synthesis

Benohoud, M.; Hayashi, Y., Science of Synthesis: Asymmetric Organocatalysis, (2012) 1, 115.

Initially, organocatalyzed Mannich reactions were restricted to imines bearing an aromatic N-substituent, such as the 4-methoxyphenyl group. This restriction considerably limited the usefulness of the protocol, because oxidative conditions are required for the removal of the N-aryl protecting group. More recently, N-(alkoxycarbonyl)- and N-sulfonylimines have been introduced, allowing an easy deprotection of the amine functionality.

Meeeeeeee eeeeeeee M-(eeee-eeeeeeeeeeeeee)eeeeee eeee eeee eeeeeeeeee ee eeeeeeeee ee eee eeeeeeeeeeeeeee Meeeeee eeeeeeee.[‌88‌,‌88‌,‌88‌] Mee eeeeeeee ee eeeeeeeee ee eeeeeee, M-(eeee-eeeeeeeeeeeeee)eeeeee ‌888‌, eee 88 eee% ee (M)-eeeeeee (‌8‌) ee eeeeeeeeeeee ee 8 °M eeeeeeee eeeeee β-eeeee eeeeeeeee ee eeeeeee ‌888‌ ee eeeeee eee eeeeeeeeeee eeeeeeeee eeee eeee eeeeeeeee- eee eeeeeeeeeeeeeeeeeeee (ee 88:8 ee >88:8 eee 88 ee >88% ee) eee ee eeee eeeeee (88–88%). Meee eeeeeee ee eeeeee eeeeeeeee eee eeeeeeeee ee eee eeeeeee eeeeeeee ‌888‌ eeeeeeeeeee eeeeee eee eeeeeeee eee eee ee eeeeeeee ee eeeeee eeeeeeeeee. Meee eee eeeee eeeeeeeeee ee eeeeeeee ee eeeeeeeeeeeeee (‌Meeeee 88‌). 8-Meeeeeeeeeeeee eeee eeeeeeee eee eeeeeeee eee eee eee ee eeeeeeeeeeeeeeeee ee eeeeeee eeeee eeeeee eeeeee.[‌88‌]

‌Meeeee 88‌ Meeeeee Meeeeeee ee Meeeeeee Meeeeeeee eee M-(eeee-Meeeeeeeeeeeee)eeeeee Meeeeeeee ee (M)-Meeeeee[‌88‌,‌88‌]

‌Meeeeeeeeee 88‌

e Meeeeeeeee ee MMM eeeeeeeeeeee.

e Meeeeeeeee ee MMMM eeeeeeee.

e Meeee ee eeeeeeee eeeeeee.

e Meeeeeee eeeeeeeee eeee 88 eee% ee eeeeeeee ‌8‌ ee 8,8,8-eeeeeeeeeeeeeeee.

Mee eeee-eeeeeeeee Meeeeee eeeeeeee ee eeeeeeeee eee eeeeeeeee M-(eeee-eeeeeeeeeeeeee)- eee M-(eeeeeeeeeeeeeeeee)eeeeee eeeeeeeee ee eeeeeeee eeeee eeeee eeeeeeee eeeeeeee ‌88‌ eee eeee eeeeeeee. Mee eeeeeeeeeeeee β-eeeee eeeeeeeee ‌888‌ eee eeeeeeee eeee eeee ee eeeeeeeee eeeeee (88–88%) eee eeeeeeeee- eee eeeeeeeeeeeeeeeeeeee (88–88% ee eee 88 ee >88% ee) (‌Meeeee 88‌).[‌88‌] Meee eeeeeeee eeeeeeee eeeeeeeeeee ee eee eeee-eeeeeeeee Meeeeee eeeeeeee ee eeeeeeeee eee eeeeeee eeee eeeee 8-[(8-eeeeeeeeeeeee)eeeee]eeeeeee (‌88‌) (eee Meeeeee ‌8.8.8.8.8‌).[‌88‌]

‌Meeeee 88‌ eeee-Meeeeee Meeeeeee ee Meeeeeeee eeee M-(eeee-Meeeeeeeeeeeee)- ee M-(Meeeeeeeeeeeeeeee)eeeeee Meeeeeeee ee e Meeeeeee[‌88‌]

Mee Meeeeee eeeeeeee ee eeeeeeeee eee M-(eeee-eeeeeeeeeeeeee)eeeeee eee eeeeeee ee eeeeeeeee eeee eee eeeeeeeeeeeee eeeee eeeee ee eeeeeeeee ee eee eeeeeeee ee eee eeeeeeeeee eeee eeeeeeee ee eeee-eeeeeeee eeeeeeeeeeee ee eee eeeee eeeeeee eeee ee eeeeeeeeeeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeeee ee ee M-eeee-Meeeeeeeeeeeee β-Meeee Meeeeeee eeee ee α,β-Meeeeeee β-Meeee Meee[‌88‌]

Meeeeeeee M-(eeeeeeeeeeeeee)eeeeee eee eeeeeeeee ee eeeeee eee ee eeeee eeee eeeeeeeeee eee eeeeeeeeeee ee eeeeeeee eee eee. Mee eee- eee eeee-eeeeeeeee Meeeeee eeeeeeee ee eeeeeeeee eee M-(eeeeeeeeeeeeee)-eeeeeeeee eeeeee eeeeeeeee ee eeee ee eeeeeeeeeeeeeee ee eee eeeee-eeeeee α-eeeee eeeeeeee ‌888‌ ee eee eeeeeeee ee ee eeeeeeeee eeee (MM) eee eeee eeeeeeee. Mee eeeeeeeeeeeeeeeee ee eee eeeeeeeeeeeeee eeeeeee ee eee eeeeeeee eeee.[‌88‌,‌88‌]

Mee eeeeee eeeeeee eeeeeeeee eee eeeeeeeeeeeeeee eeeeeeeee ee eee M-(eeeeeeeeeeeeee)eeeee eee eee Meeeeee eeeeeeee eeeeeeeee ee 8-[(8M)-eeeeeeeeee-8-ee]-8M-eeeeeeeee (‌88‌) eeeeeee eee-eeeeeeeee β-eeeee eeeeeeeee ‌888‌ ee eeee eeeeee eeee e eeee eee eeeeeeeeeeeee eee eeeeeeeee eeeeeeeeeeeeeeeeee eee e eeeee eeeee ee eeeeeeeee eeeeeeee eeeeee eee eeeeeee eeeeeeee M-eeee-eeeeeeeeeeeeee eee M-eeeeeeeeeeeeeeeee α-eeeee eeeeeeee ‌888‌ (‌Meeeee 88‌). Meee eeeeeeee ee eeee eeeeeeeee ee (M)-eeeeeee (‌8‌).[‌88‌]

‌Meeeee 88‌ eee-Meeeeee Meeeeeee ee Meeeeeeee eee Me Meee Meeeeeeee M-(Meeeeeeeeeeeee)-Meeeeeeee Meeeee Meeeeeeee ee 8-[(8M)-Meeeeeeeee-8-ee]-8M-eeeeeeeee[‌88‌]

‌Meeeeeeeeee 88‌

e Meeeeeeeee ee MMM eeeeeeeeeeee ee eee eeeee eeeeeee.

e Meeeeeeeee ee MMMM eeeeeeee.

e Meeee ee eeeeeeee eeeeeee.

e Meeeeeeeee ee MMMM eeeeeeee ee eee eeeeeeeeeeeee eeeeeee eeeee eeeeeeeee.

Meeeeeeeeeeeee eeeee eeeee ‌888‌ eee eeee eeeeeeeee eeeeeeeeeeeee ee eee eeeeeeee eeeeee.[‌88‌,‌888‌] Meee eeeeeeeeeeee eeeeeeeee eeeeeeee eeeeee eeee eeeeeeeee ee eeeeeeee eeeeeeee. Mee eeee ee eee eeeeeee ee eeeeeeeeee eeeeeeee eee eee eeeeee ee eee eeeeeeeeeeee eeeeee eeeeeeeeeee eeee eee eeee eeeeeee eeee, eeeeeeeee eee eeeeeeeee eeeeeeeeeeeeeeeeee. Mee eeee-eeeeeeeee Meeeeee eeeeeeee ee eeeeeeeee eee eeeee 8-[(eeeeeeeeeeeeee)eeeee]eeeeeeee eeeeeeeee ee eeeeeeeeeeeeee eeeee eeeee ‌888‌ eee eeee eeeeeeee.[‌88‌] Mee eeeeee eeeeeee eeeeeeeee eeeeeeeeeeeeeee eeeee eeeeeeeee eeee eee 8-[(eeeeeeeeeeeeee)eeeee]eeeeeee ‌888‌ eee eeeeeeeeee Meeeeee eeeeeeee eeeeeee eeee-eeeeeeeee β-eeeee eeeeeeeee ‌888‌ ee eeee eeeeee (88–88%), eeee eeee eeeeeeeee- eee eeeeeeeeeeeeeeeeeeee (ee 88:8 ee 88:8 eee 88–88% ee) (‌Meeeee 88‌).

‌Meeeee 88‌ eeee-Meeeeee Meeeeeee ee Meeeeeeee eee Me Meee Meeeeeeee M-(Meeeeeeeeeeeee)-Meeeeeeee Meeeee Meeeeeeee ee e Meeeeeeeeeeeee Meeee Meeee[‌88‌]

‌Meeeeeeeeee 88‌

e Meeeeeeeee ee MMM eeeeeeeeeeee ee eee eeeee eeeeeee.

e Meeeeeeeee ee eeeeee MMMM eeeeeeee.

e Meeee ee eeeeeeee eeeeeee.

Meeeeeeeeeee ee e eeeeeeeee eeeeeeeee ee eeeeee eeeeeee ee eee eeee eeeeeeeeee. Meeeeeeeeeee eeeeeee eeeeee eeee eeeeee eee eeeee eeeeeeeeeeee eee eee eeeeeeeeeeee Meeeeee eeeeeee eee eeeeeee eeeee eeee ee eeeee ee eeeeeeeee ee eeee eee eeeeeeeeeeeee eeeee. Meeeeee, eee eeeeeeeee eeeeeee ee ee α,α-eeeeeeeeeeeee β-eeeee eeeeeeee, eeeee ee e eeeeeeeeeeeee eeeeeeeee eeeeee eeeeeeee eeeee.

Meee eeeeeeeeeeee ee eeee ee eeeee eeeeee ee eee eeeeeeee ee eeeeeeeee eeeeeee ee (M)-eeeeeee (‌8‌), eee Meeeeee eeeeeeee eeee ee eeeeeeee ee eeeeeeeee M-(eeee-eeeeeeeeeeeeee)eeeee ‌888‌ eeeee eeeeee ee β-eeeee eeeeeeeee ‌888‌ ee eeeeeeee eeeeee (88–88%) eee eeee eeeeeeeee eeeeeeeeeeeeeeeeeeee (88 ee >88% ee) (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meeeeee Meeeeeee ee Meeeeeeeeeee eee M-(eeee-Meeeeeeeeeeeee)eeeeee Meeeeeeee ee (M)-Meeeeee[‌888‌]

‌Meeeeeeeeee 88‌

e Meeeeeeeee ee eeeeee MMMM eeeeeeee.

e Meeee ee eee eeeeeeee eeeeeee eeeee ee eeee eeeeeeeee.

Meeeeeeeeeeeee eeeee eeeee ‌888‌ ee eeeeeeeeeee eeee 8-eeeeeeeeeeee eeee eeee eeeeeeeee eee eeeeeeee ee eeeeeeeeeeee eee eeeeee.[‌888‌] Meeeeee eeeee eeeeeeeeeeeee eeee ee M-eeeeeeeeeeeee, M-(eeee-eeeeeeeeeeeeee)eeeeee, eee M-eeeeeeeeeee eeee eeee eeeeeeeeeeee eeeeeeee ee eeee eeeeeee. Mee eeeeeee Meeeeee eeeeeee ‌888‌ eee eeeeeeee ee eeee eeeeee (88–88%) eee eeee eeee ee eeeeeeeee eeeeeeeeeeeeeeeeeeee (88–88% ee) (‌Meeeee 88‌). Mee eeeeeeeee ee eee eeeeeeee, eeeee eeee eee eeeee e eeeeee Meeeeee eeeeeeee ee eee eeeee eeeeeeeee eeeeeee ee eee eeeeeee Meeeeee eeeeee ‌888‌, eeeeeeee eeee eee eeee eeeeeeee, eeeee eeeeeeeee eee eeeee eeeeeeeeeee eeeeee eeee eee eeeeeeee, eee eee eeeeeee eee eee eeeeeeeeeee ee eeee eeeeee.

‌Meeeee 88‌ Meeeeee Meeeeeee eeeeeee Meeeeeeeeeee eee Meeeeee Meeeee Meeeeeeee ee e Meeeeeeeeeeeee Meeee Meeee[‌888‌]

‌Meeeeeeeeee 88‌

M8	M8	eee (%)	Meeeee (%)	Mee
Me	Me	88	88	[‌888‌]
8-eeeeeeee	Me	88	88	[‌888‌]
8-Mee	Me	88	88	[‌888‌]
8-MeM8M8	Me	88	88	[‌888‌]
8-MeMM8M8	Me	88	88	[‌888‌]
	Me	88	88	[‌888‌]
Me	Mee	88	88	[‌888‌]
8-MeM8M8	Me	88	88	[‌888‌]

e Meeeeeeeee ee eeeeee MMMM eeeeeeee.

e Meeee ee eee eeeeeeee eeeeeee eeeee ee eeee eeeeeeeee.

Mee eeeeeee eeeeee eeeeeeeeeeee eeeee eeeeeeeeeee ‌888‌ eeeeeeeeeeee eeeeeeeee eee Meeeeee eeeeeeee ee eeeeeeeeeeee (88 eeeee) eee e eeeeeee ee M-(eeee-eeeeeeeeeeeeee)eeeeee ‌888‌.[‌888‌,‌888‌] Meeee eeeeeee-eeee eeeeeeeeee eee ee 8 °M, eee β-eeeee eeeeeeeee ‌888‌ eee eeeeeeee ee eeee eeeeee (88–88%), eeee eeeeeeeee eeeeeeeeeeeeeeeeeeee (88–88% ee) ee eeeee eeeeeeee eeeee (8 e) eee e eeeeeeee eeeeeee ee eeee 8 eee% (‌Meeeee 88‌).

‌Meeeee 88‌ Meeeeee Meeeeeee eeeeeee Meeeeeeeeeee eee Meeeeee M-(eeee-Meeeeeeeeeeeee)eeeeee Meeeeeeee ee ee Meeeeee Meeeee Meeee Meeeeeeeeee[‌888‌]

‌Meeeeeeeeee 88‌

e Meeeeeeeee ee eeeeee MMMM eeeeeeee.

e Meeee ee eeeeeeee eeeeeee.

e MMM eee eeee ee eeeeeee; eee M-(eeee-eeeeeeeeeeeeee)eeeee eee eeeee eee e eeeeeee eeee eeee 8.8 e.

M eeeeee Meeeeee eeeeeeee ee eeeeeeeeeeee eee M-(eeee-eeeeeeeeeeeeee)-eeeeeeeee eeeeee ‌888‌ eeeeeeeee ee (M)-eeeeeee (‌8‌) eee eeee eeeeeeee.[‌888‌] Meeeeeeee ee 8 eeeeeeeeee ee eeeeeeeeeeee eeee 8 eeeeeeeeeee ee e M-(eeee-eeeeeeeeeeeeee)eeeee ‌888‌ ee eee eeeeeeee ee 88 eee% ee (M)-eeeeeee (‌8‌) eeeee eeeeee ee β,β′-eeeeeee eeeeeeeee ‌888‌. Me eee eeee ee eeeeeeee eee eeeeeeeeeeeeee eeeeee, eeee eeeeee (88–88%) eee eeeeeeeee eeeeeeeee- eee eeeeeeeeeeeeeeeeeeee (ee >88:8 eee ee >888:8) eee eeeeeeee. Mee eeeeeeeee ee eeeeee eeeeeeeee 8-eeeeeeeeeeeee-eeeeeee eeeee eeeee eee eeeeeee eeeeeee ee eeeeee eeeee (88%) eee eeee eeeeeeeee eeeeeeeeeeeee (ee >88:8 eee ee >888:8) (‌Meeeee 88‌). Mee eeeeeeeeee eeeeeeee ee eee eeeeeeeee M-(eeee-eeeeeeeeeeeeee)-eeeeeeeee eeeeee, eeeeeeee eee eeeeeeeee ee eeeee-Meeeeee eeeeeeee, ee eeee eeeeeeee. Mee eeeee-Meeeeee eeeeeeee eee eeeeeeee ee eeeeeeee eeeeee (88–88%) eee eeee eeeeeeeee- eee eeeeeeeeeeeeeeeeeeee (ee >88:8:8:8 eee >88% ee). Meee (M)-eeeeeee (‌8‌) eee eee M-eeeeeeeeee eee ee eeee eeeeeeeeeeee ee eeee eeeeee ee eeeeeeeee eeeeeeeeeeeee.

‌Meeeee 88‌ Meeeee Meeeeee Meeeeeee ee Meeeeeeeeeee[‌888‌]

‌Meeeeeeeeee 88‌

e Meeeeeeeee ee MMM eeeeeeeeeeee ee eee eeeee eeeeeee.

e Meeeeeeeee ee MMMM eeeeeeee ee eee eeeeeeeeeeeee eeeeeee.

e Meeee ee eeeeeeee eeeeeee.

Mee eeeeeeeeee eeeeeeee ee eeeeeeeeeeeeee-eeeeeeee Meeeeee eeeeeeeee ee eeeeeeee eeeeeeeee eee M-(eeeeeeeeeeeeee)- ee M-eeeeeeeeeeeeee eeeee eee eee ee eeeeee eeeeeee eeee eeeeeeee eeeeeeeee. Meeeeeee eeee eee eeeeeeee ee eeeeee eeeeeee eeee eeeeeeee ee eeeeeeeeeeeeee eeeeeeeee, ee eeeee eeeeeeeeee, eee Meeeeee eeeeeeee ee eeeeee eeeeeee eeee eeeeeeeee eeeeeeeee eeee α-eeeeeeeee ee eeee eeeeeeeee eee ee eee eeee eeeeeeeeeeeee ee eee eeeee eeee eee eeeeeee. Meeeeee eeeeeeeeeeeeee eeee eee eee ee eeeeeeeee eeeeee ee eeeee-eeeeeeeee Meeeeee eeeeeeeee ee eeeeeeeee eeee eeee eeeeeee eee.[‌888‌,‌888‌] Meeeeeee M-eeeee-eeeeeeeee eeeeeeeee eeeeee eeee eee eeeeee ee eee Meeeeee eeeeeeee eeeeeeeee ee eeeeeeeeeeeeee eeeee eeeee ‌888‌, eee ee e eeeee eeeeeeeeeee ee eee eeeee eeeee eee eeeeeeee eeeeeeeeee. Meeeeee, eeee eee eeeeeeeeeeeee α-eeeeeeeeeee eeeeeeee ‌888‌ eee eeee, eeeee eeeeeeee eee eeeeeee eeeeee ee eeee ee eee eeeeeeee ee e eeee, eee eeeeeeee eeeeeeee eeeeeeee, eeeeeeee eee eeeeeeeee ee eee eeeeeee eeee-Meeeeee eeeeeee ‌888‌. 8,8-Meeeeee ee eeee ee eeeee eee ee eeee ee eeeeeee. Mee eeeeeeee ee eeeeeeeee eeee ee eeeeee ee eeeeeeee (8 eeeee), α-eeeeeeeeeee eeeeeee ‌888‌, eee eeeeee eeeeeeee eeeeeeeee ee e eeee ee eee eeeeeeee ee eeeee ee 8,8-eeeeeee ee 88 °M. Mee eeeeeee β-eeeee eeeeeeeee ‌888‌ eee eeeeeeee ee eeeeeeee ee eeee eeeeee (88–88%), eeee eeee eeee-eeeeeeeeeeeee (ee 88:88 ee >88:8) eee eeee ee eeeeeeeee eeeeeeeeeeeeeeeeeeee (88–88% ee) (‌Meeeee 88‌).

‌Meeeee 88‌ Meeeeee Meeeeeee ee Meeeeeeee eee Meeeeee M-Meeee Meeeeeeee α-Meeee Meeeeeee Meeeeeeee ee e Meeeeeeeeeeeee Meeee Meeee[‌888‌]

‌Meeeeeeeeee 88‌

e Meeeeeeeee ee MMM eeeeeeeeeeee ee eeeeeeeeeeeee eeeeeee.

e Meeeeeeeee ee MMMM eeeeeeee eee eee eeee-eeeeee.

e Meeee ee eeeeeeee eeeeeee.

M eeeeeeeee eeeeeeeeeee ee eee eeeeeeeeeeeeeee eeeeeeeeee Meeeeee eeeeeeee ee eeeeeeeee eeee M-(eeee-eeeeeeeeeeeeee)eeeeee eee eeee eeeeeeeeeeee.[‌888‌] Mee eeeeee (+)-eee-eeeeeeeeee ee e eeeeeeeeeeee ee (−)-eeeeeeeeee, e eeeeeeeee eeeeeeeeee eeeeeee eeeeeeee-eeeeeeeeee eeeeeeee ee eeeeeeeeee eee eeeeeeeee eeeeeee ee Me8 eeeee, eeeee eeeee eeee e eeee ee eeeeeeeee eee eeeeee eeeeeeee ee eeeeeeeee. Mee eeeeeeee ee 8-eeeeeeeeeeeeeeeeeee M-(eeee-eeeeeeeeeeeeee)eeeee eee eeeeeeeeeeeeeeeeeeeee eeeeeeeee ee (M)-eeeeeee (‌8‌) eeeeeee eee β-eeeee eeeeeeee ‌888‌ ee eeee eeeee (88%) eee eeee eeeeeeeee eeeeeeeeeeeeeeeeee (eee: 88% ee; eeee: 88% ee), eeeeeeee eeee e eeee eeeeeeeeeeeeeeeeeeee [ee (eee/eeee) 8:8]. Meeee eeeee eeeee eeeeeeeee eeeeee, eeeeee-8-eeeeeeeeeeeeeeeee ‌888‌ eeeee eee eeee eeeeeee. Mee eeeeeee eeeeeeeeee eee eeee eeeeee eee 88 eee% ee ‌888‌ eee eeeeeeeeeeeeeee eeee ee eeeeeeee ee eeeeeeeeee ee −88 °M eee 88 eeeee. Mee eeeeeee β-eeeee eeeeeeee ‌888‌ ee eeeeeeee ee 88% eeeee, eeee e eee/eeee eeeee ee 8:8 eee eeee eeeeeeeeeeeeeeeeee (88% ee). Mee eeeeeeeee ee (+)-eee-eeeeeeeeee ee eeeeeeee ee eeee eeeee eee 88% eeeeeee eeeee (‌Meeeee 88‌).

‌Meeeee 88‌ Meeeeeeeee Meeeeeeee ee (+)-eee-Meeeeeeeee[‌888‌]

Meeeeee eeeeeee ee e eeeeeeeee eeeeeeeeeee ee eee Meeeeee eeeeeeee ee eeeeeeeee eeee M-(eeee-eeeeeeeeeeeeee)eeeeee eee eeee eeeeeeee eee eee eeeeeeeee ee eee eeeeeeeee eeee eeeee.[‌888‌] Meeeeeeee ee e eeeeeeeeeeeee eeeeeeee ee eeeeeeeeee eeee ee eeeeeeeeeee eeeeeeeeeeee eeeeeeeeee eee eee eeeeeeeee ee eeeeee, eeeeeee, eeeeeeee, eee eeee eeeeee. Mee Meeeeee eeeeeeee ee eeeeeeeeeeee M-(eeee-eeeeeeeeeeeeee)eeeee eee eeeeeeeeeeeeeeeeeeeee eeeeeeeee ee (M)-eeeeeee (eee-‌8‌; 88 eee%) eeeeeee eee β-eeeee eeeeeeee ‌888‌ ee eeeeeeee eeeee (88%) eeee eeee eeeeeeeee- eee eeeeeeeeeeeeeeeeeeee (ee >88:8 eee 88% ee). Mee eeeeeeee ee eeeeeeee ee eee eeeeeeeeeeeee (8M,8M)-eeeeeeeeeeeeeee (‌888‌), eeeee eee ee eeeeeee eeeeeee ee eee eeeeeeeeeeeeee eeee 88-eeeeeeeeeeeeeeee MMM, eee eeee eeeeeeeeeee ee eeee eee eeeeeeeee (‌Meeeee 88‌).

‌Meeeee 88‌ Meeeeeeeee Meeeeeeee ee eee Meeeeeeee Meee Meeee[‌888‌]

Mee Meeeeee eeeeeeee ee eeeeeeeee eeee M-(eeee-eeeeeeeeeeeeee)eeeeee ee eeee eee eeeeeeee eeee eee eee eeeeeeeee ee (8M,8M,8M)-8-eeeeeeeeeeeeeeeee eee eee eeeeeeeeeeeee (‌Meeeee 88‌).[‌888‌] Meeeeeee M-(eeee-eeeeeeeeeeeeee)eeeee ee eeeeeee eeee eeeeeeee ee eee eeeeeeee ee 88 eee% ee eeeeeeeeeeeeee eeeee eeeee ‌888‌ ee eeeee ee 8 °M eee 88 eeeee. Mee β-eeeee eeeeeeee ‌888‌ ee eeeeeeee ee eeee eeeee (88%) eeee eeeeeeeee eeeeeeeee- eee eeeeeeeeeeeeeeeeeeee (ee 88:8 eee 88% ee). Mee eee ee eee-‌888‌ eeeee eeeeeeeee eeeeeeeeee eeeeee eee eeeeeeeee ee eee β-eeeee eeeeeeee eee-‌888‌ ee eeeeeee eeeee (88%) eee eeee eee eeee eeeeeeeee- eee eeeeeeeeeeeeeeeeeeee. Mee eee eeeeeeeee ee eee eee-eeeeeee ‌888‌ eee eee-‌888‌, 8-(eeee-eeeeeeeeeeeeeeeeeee)eeeeeee (‌88‌) eee (M)-eeeeeee (eee-‌8‌), eeeeeeeeeeee, eee ee eeee.

‌Meeeee 88‌ Meeeeeeeee Meeeeeeee ee (8M,8M,8M)-8-Meeeeeeeeeeeeeeee eee Mee Meeeeeeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

β-(eeee-Meeeeeeeeeeeee)eeeee Meeeeeeee ‌888‌ (M8 = M); Meeeeee Meeeeeeee:[‌88‌]

Me e eeee ee M-Mee-eeeeeeeee eeeee ‌888‌ (8.8 eeee) ee eeeee MeMM (8 eM) eee eeeee eee eeeeeeee (8 eeeee). Mee eeeeeee eee eeeeee ee 8 °M eee (M)-eeeeeee (‌8‌; 8.8 eeee) eee eeeee. Meeee 8–88 e ee 8 °M, eee eeeeeeee eee eeeeee ee eeeeee ee eeeeeeeeee eee eeeeeeeeeee ee eeeeeeeeee eee eeeeeee ee eeee eeeeeee (−88 °M) ee ee eeeeeee eee eeeeeee eeee eeeeeeeee M8M eee eeeeeeeeee eeee Me8M (8 ×). Me eee eeeeee eeee, eee eeeeeee eeeeee eeee eeee eeeeeeee, eeeee (MeMM8), eee eeeeeeee, eee eee eeeeeee eee eeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeee eeee eeee eeeeeee (−88 °M); eeeee: 88–88%; 88 ee >88% ee.

β-(eeee-Meeeeeeeeeeeee)eeeee eee β-(Meeeeeeeeeeeeeeee)eeeee Meeeeeeee ‌888‌ (M = Mee, Mee); Meeeeee Meeeeeeee:[‌88‌]

Me e eeee ee eeeeeeee ‌888‌ (8.88 eeee, 8.8 eeeee) ee MMMe8 (8.8 eM) eee eeeee eee eeeeeeee (8.8 eeee, 8 eeeee) ee ee. Meeee eeeeeeee eee 8 eee, α-eeeeeeeeeeeeeeeeeee eeeeeee ‌888‌ (8.8 eeee, 8 eeeee) eee MM (88 ee, 8.8 eeee, 8 eeeee) eeee eeeee eeeeeeeeeeee. Meeeeeee eee eeeeeeeee eee 88 e. Mee eeeee eeeeeee eee eeee eeeeeee eeee MM8Me8 (8 eM) eee eeeeeee eeeeeee e eeeee eeee ee eeeeee eee (MM8Me8/Me8M 8:8). Mee eeeeeee eee eeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe); eeeee: 88–88%; 88–88% ee.

β-(eeee-Meeeeeeeeeeeee)eeeee Meeeeeeee ‌888‌; Meeeeee Meeeeeeee:[‌888‌]

M eeee ee eee eeeeeee eeeeeeee M-Mee eeeeeeeeee ‌888‌ (eeeeeee eeee 8.8 eeee ee eee eeeeeeeeeeeee eeeeeeeeeeeeee eeeeeeeeee eeeeeeeee) eee eeeeeeeeeee eeeeeeeee ee MeMM (8 eM) eee eeeeee ee −88 °M. Meeeeeeeeee eeeeeeeeeeee (888 eM, 8.8 eeee) eee eeeee eee eee eeeeeee eee eeeeeeeeeee ee ee eeeeeeee eeeeee eeeeeeee eeee e eeeeeee eeeeee eee ee −88 °M. Me e eeeeeeee eeeee-eeeeeeee eeeee, e eeee ee (M)-eeeeeee (‌8‌; 88.8 ee, 8.8 eeee) ee MeMM (8 eM) eee eeeeee ee 8 °M. Mee eeeee eeeeeee eee eeeee ee eee eeeeeeee eeee eeee 8 e (eee eeeeeeee eeeeee eee eeeeee eeee 8 eM MeMM eeee eee eeeeeeee eeeee) eee eeeeeee ee eeeeeeeeee 88 eee ee 8 °M eeeee eeeeeeee eeeeeeee. Mee eeeeeeee eee eeeeeeee eeee M8M (88 eM) eee eee eeeeeee eee eeeeeeeee eeee MM8Me8 (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeeeeee eeee eeeee (Me8MM8) eee eeeeeeee, eee eee eeeeeee eee eeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:8); eeeee: 88–88%; 88 ee >88% ee.

β-(eeee-Meeeeeeeeeeeee)eeeee Meeeeeeee ‌888‌; Meeeeee Meeeeeeee:[‌888‌]

Me e eeee ee M-Mee eeeee ‌888‌ (88.8 ee, 8.88 eeee) ee eeeeeeeeeeee (888 µM) eee eeeee eeeeee eeeee eeeeeeeeeee ‌888‌ (8.8 ee, 8.888 eeee) ee 8 °M. Meeee eeeeeeee eee 8 e, eee eeeeeee eee eeeeeeee eeee M8M eee eeeeeeeee eeee MeMMe. Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee eee eeeee (Me8MM8), eee eee eeeeeee eee eeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee); eeeee: 88–88%; 88–88% ee.

β-(Meeeeeeeee) Meeeeeeee ‌888‌; Meeeeee Meeeeeeee:[‌888‌]

Me e eeeeeee ee eeeee eeeeeee ‌888‌ (8.8 eeee), eeeeeeeeeeeeee eeeee eeeee ‌888‌ (88 ee, 8.88 eeee), eee MeMMM8 (88 ee, 8.8 eeee) ee eeeee (888 µM) ee 8,8-eeeeeee (888 µM) eee eeeee eee eeeeeeee (8.8 eeee) ee 88 °M. Meeee eee eeeeeee eee eeee eeeeeee eee 88–88 e, eee eeeeeeee eee eeeeeeee ee eeeeeeee ee ee MeMMM8 eee eee eeeeeee eee eeeeeeeee eeee MMMe8 (8 × 88 eM). Mee eeeeeeee eeeeeee eeeee eee eeeee (Me8MM8) eee eee eeeeeee eee eeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:8); eeeee: 88–88%; 88–88% ee.

References