Science of Synthesis

Zaidlewicz, M.; Pakulski, M. M., Science of Synthesis: Stereoselective Synthesis, (2011) 2, 102.

α,β-Unsaturated ketones can be cleanly reduced to allylic alcohols by boranes/oxazaborolidines, although uncatalyzed hydroboration–oxidation leads to 1,2-diols or saturated alcohols.[‌294‌] α-Substitution is helpful in achieving high chemo- and stereoselectivity.

Meeeee eeeeee eeee ee eeeeeeeee eeeeee eeee eee eeeeeee ee eeeee eeeeeeeeeeee ee eeeee eeeeeeeeeeeee ee eee eeeeee eeee.[‌888‌] Mee eeeeeee-eeeeeeeeee eeeeeeeeeee eeeeeeeee eee eeeeeeeee ee eeeeeeee eeeeee eeeeeee, e.e. ee eee eeeeeeeee ee eeeeeee ‌88‌ (‌Meeeee 88‌).[‌888‌–‌888‌]

‌Meeeee 88‌ Meeeeeeeeeeeeeeeee Meeeeeeee ee e Meeeeee eeee Meeeee–Meeeeeee Meeeeee Meeeeee/Meeeeeeeeeeeeee[‌888‌]

Meeeeeeeeeeeeee-eeeeeeeee eeeeeeeee ee eee eeee eeeeeeeee eeeeeeeee α-eeeeeeeee eeeeeee eee eeee eeee eeeeeeee. Meeeeeeee, Meeee[‌888‌] eeeeeeee eee eeeeeeeee ee eee eeeeeeeeeee eee eeeee eeeeee 8-eeeeeee-8-eeeeee eeeee eeeeeeeeeeeeee/eeeeeeeeeeeeeee ‌88‌ (M8 = MM8MMM) ee −88 °M ee 88% eeeee eee 88% ee. Meeee, eeeee eeeeeeeeeeee ee eee eeeeee eeeeee, eeeeee ee eeeeee, eeeeeeeeeee, eee eeeeeee, eeeeee–M,M-eeeeeeeeeeeeee/eeeeeeeeeeeeeee (M)-‌88‌ (M8 = Me) eee eeeee ee eeeeee α-eeeeeeeee eeeeeee, eeeeeeeee eee eeeeeeeeeeeee eeeeeee eeeeeeee (88–88% eeeee, 88–88% ee) eee 8-eeeeeeeee-8-ee-8-ee (88% eeeee, 88% ee) (‌Meeeee 88‌).[‌888‌] Mee eeeeeeeeeeeeee eee eeee eeee ee e eee eeee ee eee eeeeeeeee ee eee M88 eeeeeeeeeee eeeeee ee eeeeeeeeee [(8α,88M)-eeeeeeeeeeeeeeeeeeeeeeee] ee 88% ee.

‌Meeeee 88‌ Meeeeeeee ee α-Meeeeeeee Meeeeee eeee Meeeee–M,M-Meeeeeeeeeeeee/(M)-M-Meeeeeeeeeeeeeeeeeeee[‌888‌]

‌Meeeeeeeeee 88‌

e 88 eee% eeeeeeee, eeee eeeeee eeeeeeee (8.8 e), eeee 8 e.

e 88 eee% eeeeeeee, eeee eeeeee eeeeeeee (8.8 e), eeee 8 eee.

Meeeeeeeeee ee eee eeeeeeeee ee eeeeeee eeeeee eeeeeeeeee eeeeeeee eeeeeeeeeeeee eeeeee eeeee eeeeeee ee eeeee eeeeeeeee, eee eee eeeeeee eeeeeeeeeeee. Mee eeeeeee, eeee eeeeeee eeee eeeeee–eeeeeeee eeeeeee eeeeeee/(M)-‌88‌ (M8 = Me), e eeeeeeeeeeeee eeeeeeeeeeee eeeee ‌88‌ eeeee eeeeeee ‌88‌ ee 88% ee;[‌888‌] ee e eeeee-eeeee eeeeeeeeeee eee eeeeeeee ee eeeeee eee e eeeee eeeeee ee eeeee eeeeeeeee eee eeeeeeeeeee ee 88.8% ee (‌Meeeee 88‌). Mee eeeeeeee ee eeeee eee eeeeee ee eeeeeee ee eeeeeee eeeeeeeeeeeee ee eee eeeeeee eeeeee eee eeeeeeeeeeeee ee eee eeeeee eeee. Me eeeeeeee eeeeeeeeee e eeeeeeeeee eeeeeeeeeee eeeeeee ee eee eeeeeeee eeeee eeeeeeeee eeeeeeeee eeee eeeee eeeeeeeeeee.[‌888‌] Me eee eeeeeeeee ee 8-(8-eeeeeeeeeeeee)eee-8-ee-8-eee eeee eeeeee/(M)-‌88‌ (M8 = Me), eee eeeeeeeeeee eeeee eee eeeeeee eeeeeeeeeee ee eeee eeeeee.[‌888‌] Me eee eeeee eeee, e eeeeee eeeee- eee eeeeeeeeeeeeeee eeeeeeeee ee eeeeeeeeeee β-eeeeeee eeeeeeee ‌88‌ eee eeee eeeeeeee ee eee eeeeeeeee ee eeeeee ‌88‌ eeee eeeeee/M-eeeee-M-eeeeeeeeeeeeeeee/(M)-‌88‌ (M8 = Me) eeeeeee eee eeeeeeeee (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meeeeeeee ee Meeeee eeee Meeeee/M-Meeeeeeeeeeeeeeeeeeee[‌888‌,‌888‌]

Meeeee/eeeeeeeeeeeeeee eeeeeeeee ee eeeeee eee eeee eeee eeee ee eee eeeeeeeee ee eeeeeee eeeee eeeeeeeeeeee eeeeee eeeeeeeee, eeeeeeeee eeeeeeeeee,[‌888‌] eeeeeeee,[‌888‌] eeeeeeeeeee,[‌888‌] 8-eeeeeeeeeee eeeeeeeee eeeee,[‌888‌] (+)-eeeeeeeee,[‌888‌] eeeeeeeeee M8,[‌888‌] eeeeeeeeeee,[‌888‌] eeeeeeeeee M,[‌888‌] (+)-eeeeeeeeeeee,[‌888‌] eee eeeeeeeeeee M.[‌888‌]

α,β-Meeeeeeeee eeeeeee eee eeeeeee eeeeeeeee eeeeeee ee eeeeeeeeeeeeeee eee e eeeee eeeeeeeeeee eee eeeeeeeee eeeeeeeee. Mee eeeeeee eeeee eeeeeee ee e eeeee eeeeeeeeeee eeeeeeeeee ee eee eeeee eeeeeeee eeeeeeeeeee, e.e. eeeee,[‌888‌] eeeeeee,[‌888‌,‌888‌] ee eeeeeeeeeeeee.[‌888‌] Meeeeee, eee (eeeeeeeeeeeeee)eeeeeee eeeeee eeeeee eee eeeeee ee e eeeee eeeee.[‌888‌] Meeeeeeeeee ee eee eeeeeeeee ee eeeee eeeeeee eeeeeeeee eeee e eeee eeeee eeeeeeeeeee ee eee eeeee eeee ee eee eeeeeeee, e.e. (eeeeeeeeeeeeee)eeeeee eeeeeee ee eeeeee. Mee Meeee–Meeeee–Meeeeee (MMM) eeeeeeeee ee α,β-eeeeee eee eeee eeeeeeee ee eee eeeeeeeee ee eeeeeeeeeeeeee M,[‌888‌] eeeeeeeeeeeeeeeee,[‌888‌] eeeeeeeeee,[‌888‌] eee 88-eeeeeeeeeeeeee.[‌888‌]

8,8-Meeeeeeee eeeeeee eeee eeeeee/eeeeeeeeeeeeeeee eeeeeee eeeee ee eeee eeeee. Mee eeeeeee, eeeeee ee eeeeeeeeeee eeee eeeeee–eeeeeeee eeeeeee eeeeeee/‌88‌ (M8 = Me) eeee eeeeeeeeeeee (eeeee/eeeeeee 88:88).[‌888‌]

8,8-Meeeeeeee eee ee eeeeeeeeeee eeee eeeeeeeeeeeeee/‌88‌ (M8 = Me). Meee eee eeeeeeee ee eeeeeeee ee eee eeeeeeee ee (M)-8,8-eeeeeeeeeeeeeeee [(M)-‌88‌] eeee eeeeeeeeeeee eeee eeeee eeeeeeee eeeeeeeeee, eee eeeeeeee ee M,M-eeeeeeeeeeeeee eeeeeee eeeeeee eeeeeeeeeee ee eee eeeeeeeee ee Meeeeeʼe eeeeeeee ‌88‌ ee eeeeeee ‌88‌ (‌Meeeee 88‌).[‌888‌,‌888‌]

Meeee eeeeeeee ee eee MMM eeeeeeeee ee 8,8-eeeeeeeee eee eeeeeeeee β-eeeeeee eeeeeee ee 8,8-eeeee eeee eeee eeeeeeeee.[‌888‌,‌888‌,‌888‌] Mee MMM eeeeeeeee eee eeeeeeeee-eeeeeeeee eeeeeeee eeeeeeeeeeeee ee eeeeeeeeee 8,8-eeeeeeeee eeee eeee eeeeeeee.[‌888‌] Meeeee eeeeeeeee ee 8,8-eeeee eeeee eee ee eeeeeeee. Mee eeeeeeee eeeeeeeeeeeee eeeeeeee 8-eeeeeeeeee-β-eeeeeee eeeeeee ee eeee eeeeeeeeeee eeee eeee e eeeeee eeeeee eeeeeeeeeee. Mee MMM eeeeeeeee ee eeeeeee β-eeeeeee eeeeeee ‌88‌ (M8 = Me, eMe) eeeeeeee eeeee eeeeeeeeeeeeee eeeeeee ee eee eeeeeeee, eeeeeeeee eee- eee eeee-‌88‌ ee eeee eeeeeeeeeeee eeeeee (‌Meeeee 88‌).

‌Meeeee 88‌ Mee Meeeeeeee ee 8,8-Meeeeeeee eee Meeeeeeee β-Meeeeee Meeeeee eeee Meeeeeeeeeeeee ee Meeeee–Meeeeeee Meeeeee/Meeeeeeeeeeeeeee[‌888‌,‌888‌]

‌Meeeeeeeeee 88‌

Mee eeeeeeeee ee α-eeee eeeeeee, eeeeeeeee ee eeeeee ee eeeeeeeeeeeeeeee eeeeeeeee β-eeeee eeeeeeee, eee eeee eeeeeeeeeee eeeeeee. Meeeeeeee eeeeeeeeeeeee,[‌888‌] eeeeeeeeee eeeeeeee eeeeeeeeeeeee,[‌88‌] eee eeeeee/eeeeeeeeeeeeeee eeeeeeeee[‌888‌–‌888‌] eeee eeee eeeeeee ee eee eeeeeeeee ee eeeee eeeeeeeee. Mee eeeeeee, eee eeee eeeeee eeeee eeee ee eee eeeeeeeee ee eeeeeeeeeeeee,[‌888‌] eeeeeeeeee ee γ-eeeeeeeee,[‌888‌] eee eeeeeeeeeeee β-eeeee eeeeeee ‌88‌,[‌888‌] eee (M,M)-eeeeeeeeee ‌88‌[‌888‌] (‌Meeeee 88‌).

‌Meeeee 88‌ Meeeee/Meeeeeeeeeeeeee Meeeeeeee ee α-Meee Meeeeee[‌888‌,‌888‌]

Meeeeeeeeeee eeeeee ee eee eeeee-eeeee eeeeeeeee ee eeeeee ‌88‌ eeeeeee ee eee eeeeeeee eeee ee eee eeeeeeeee eee eee eeeeeeeeeee. Mee eeeeeeeee 88-eeee eeeeeeee eeee ee eee eeee eeeee eee eeeeeeeee eeeeeeee. Mee eeeeeee eeeeeeeee eeeeee–M-eeeee-M-eeeeeeeeeeeeeeee eeeeeee ee eeee eeeeeeeee eee eeeeeeeeee eee eee MMM eeeeeeeee ee eeeeeee eeeeeeeeeeeeee eeeeeee, eeee ee α-eeeeeeeeeee eee α-eeeeeee eeeeeee, α-eee eeeeeee, eee α-eee eeeeeeee eee eeeeeeee.[‌888‌] Mee MMM eeeeeeeeee ee eeeeeeeeeeee eee eeeeeeee[‌888‌] eee eeeeeeeee α-eee eeeeeeeeeeee,[‌888‌] eee eeeeeeeeeeeeeeee ee eeeeeeeeeeeeee eeee-eeeeeeeee,[‌888‌] eee eeeeeee eeeeeeeeee ee eeeeeee eeeeeee, eee eeeeeee ee eee eeeeeeeee ee (M,M)-eeeeeeeee,[‌888‌] e eeee eeeeeee, eee eeeeeeee M,[‌888‌] e eeeeeeeeee eeeeeeeee, eeee eeee eeee eeeeeeee. Meeeeeeeeeeeeeeeee ee eee eeeeeeeeee ee e eeeeeeeeeeeeee eeeeeeeeee eeeee ee eeeeeeeeee ee eee eeeeeeeeeee ee eee eeeeeeeeee eeeee eeee.[‌888‌]

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 88/8, 888.