Science of Synthesis

Pineschi, M.; Boldrini, C., Science of Synthesis: Advances in Organoboron Chemistry towards Organic Synthesis, (2019) 1, 202.

Nonactivated epoxides are less reactive in the borylative ring-opening reaction than their vinylic or propargylic counterparts. Nonetheless, copper catalysis allows the SN2 ring opening with bis(pinacolato)diboron (‌2‌) and bis[(pinacolato)boryl]methane (‌43‌), yielding 1,2- and 1,3-hydroxyboronates, respectively, which are of synthetic importance given their possible applications.[‌11‌,‌12‌]

Mee eee eeee eeeeeee eeee eee[(eeeeeeeeee)eeeee]eeeeeee (‌88‌), eeeeee(M) eeeeee ee eee eeee eeeeee ee eeeeee. Mee eeeeeeee eeeeeeee e eeee (eeeeeee eeee-eeeeeeee), eeee eeeeeeeeeeee, eee eeee eeeeeeee eeeee, eee ee eeeeeeee ee eeeeeee ee eeeeeeee (‌Meeeee 88‌).[‌88‌] Mee eeeeeeee eeeee eeee ee eeee eeeeee eee 8,8-eeeeeeeeeeeeeeee (e.e., ‌88‌) eeee eeee eeeeeeee- eee eeee-eeeeeeeeee eeeeeeeeee ‌88‌. 8,8-Meeeeeeeeeeee eeeeeeee ‌88‌ eeeee ee eeee eeee eee eeeeeeeeeeeeeee eeee, eee 8,8-eeeeeeeeeeeee eeeeeeee ee eee eeeee eeeee eee eeee eeeeeeeeee eee ee eeeeeeee eee eeeeeeee eee eeeeee eeeee-eeeeeeeeeee eeeeeeee. Meeeeeeeeeeee, 8-eeeee-M-eeeeeeeeeeeeee eeee eeeeee eeeee eeee eeeeeeeee eeeeee, eee eeee ee eee eeee eeeeeee eeeeeeee eee eeeeeeeeee.[‌88‌] Me ee eeeeeeeee ee eeeee eee eeee eee eeee eeeeeee eeeeee eeeeee ee eee eeee-eeeeeeee eeeeee, ee eeeeee eeeeeee ee M8 eeeeee eeeee eeeeeeeeeeeee ee eee eeeee eeeeeee.[‌88‌]

‌Meeeee 88‌ Meeeee Meeeeeeee Meeeeeeeee Meee Meeeeee ee Meeeeeee eeee Mee[(eeeeeeeeee)eeeee]eeeeeee[‌88‌]

‌Meeeeeeeeee 88‌

M8	M8	Meeee (%)	Mee
MM8MMe	M	88	[‌88‌]
8-MeMM8M8MMM8	M	88	[‌88‌]
8-MeMM8M8MMM8	M	88	[‌88‌]
8-MeM8M8MMM8	M	88	[‌88‌]
8-MM8M8MMM8	M	88	[‌88‌]
8-MM8M8MMM8	M	88	[‌88‌]
8-MeM8MM8M8MMM8	M	88	[‌88‌]
8-MeM8M8MMM8	M	88	[‌88‌]
8-Me-8-MeM8M8MMM8	M	88	[‌88‌]
MM8MMe	M	88	[‌88‌]
	M	88	[‌88‌]
8-MeMM8M8MM8	M	88	[‌88‌]
	M	88	[‌88‌]
MM8MMe8	M	88	[‌88‌]
8-MeM8M8MMM8	M	88	[‌88‌]
Me	M	88	[‌88‌]
8-MeMM8M8MMM8	Me	88	[‌88‌]
	Me	88	[‌88‌]
		88	[‌88‌]
	Me	88e	[‌88‌]

e Meeeeeee eeeeeeeee ee 88 °M.

Meeee eeeeeee eeeeeeee eeeeeeeeee, eee eeeeee eeee eeeeeee ee eeeeeeee (e.e., ‌88‌) eeee eeeeee eeee eeeeeee eeeeeeee. Mee eeeeeeeeeee ee eeeeee(M) eeeeee eee eeeeeee eeee-eeeeeeee eeeeeeeeeee eeeeeeeee eee(eeeeeeeeee)eeeeeee (‌8‌) ee eeee eee eeee eeeeeee eee eee eeeeeeee 8,8-eeeeeeeeeeeeeeee (e.e., ‌88‌), eee eeeee eeee eeeeeeeeeeee eee eeee eeeeeeee eeeee eee eeeeeeee eee eee eeeeeeee ee eeee eeeee (‌Meeeee 88‌).[‌88‌] Mee eeeeee eeee eeee eeee ee eeee, eee eee eeeee ee eee eeeeeeee ee eeeeeeee ee eeee-eeeeeeeeee eeeeeeee eeeeeeeeee ‌88‌, eeee eeee eeeee eeeeeeee ee eee-eeeeeeee eeeeeeeeeee eee eeee eeee eeee eeeee eeeeeeeeeeee. Meeeeeeeeee, 8,8-eeeeeeeeeeeee eeeeeeee eee eee eeeeeeee eeeee eeee eeeeeeeee eeeeee. Meee eeeeeee eeeeee eeeeeeeeeee ee eee eeee-eeeeeeee eeeeee ee eee eeeeeee, eeee eeeeeeeee ee eeeeeeeeeeeee ee M8. Meeeeee eeeeeee ‌88‌ eee eeee ee eeee ee eeee eeeeeeee.

Mee eeeeeeee eeeeeeee eeeeeee M—M eeee eeeeeeeee ee 8,8-eeeee, Meeeee–Meeeeee eeeee eeeeeeee eeee eeee eeeeeee, eee Meee–Meeee–Mee eeeee eeeeeeee eeee eeeeee.[‌88‌]

‌Meeeee 88‌ Meeeee-Meeeeeeee MM8 Meeeeeeeee Meee Meeeeee ee Meeeeeee[‌88‌]

‌Meeeeeeeeee 88‌

M8	Meeee (%)	Mee
MMe	88	[‌88‌]
8-MeMM8M8M	88	[‌88‌]
8-MeMM8M8M	88	[‌88‌]
8-MeM8M8M	88	[‌88‌]
8-M8MM8M8M	88	[‌88‌]
	88	[‌88‌]
	88	[‌88‌]
8-MeM8M8M	88	[‌88‌]
8-MeM8M8M	88	[‌88‌]
8-MM8M8M	88	[‌88‌]
8-Me-8-MeM8M8M	88	[‌88‌]
8-MeM8MM8M8M	88	[‌88‌]
8-eMeM8MM8M8M	88	[‌88‌]
	88	[‌88‌]
Me	88	[‌88‌]
8-MeMM8M8	88	[‌88‌]

‌Meeeeeeeeee 88M‌

Meeeeeeeeeee Meeeeeeee

8,8-Meeeeeeeeeeeeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

M Meeeeee eeee eeeeeeee eeee e eeeeeee eee eee eeeeeee eeee MeM (8.8 ee, 8.88 eeee, 88 eee%), e-MeMMe (88 ee, 8.8 eeee, 8 eeeee), eee eee[(eeeeeeeeee)eeeee]eeeeeee (‌88‌; 888 ee, 8.8 eeee). Mee eeeeee eee eeeeeeeee eee eeeeee eeee eeeee (8 ×). Meeee eeeee eee, eeeee MMM (8.8 eM) eee eeeee eee eee eeeeeee eee eeeeeee ee 88 °M eee 88 eee. Meee, eeeeeee ‌88‌ (8.8 eeee) eee eeeee eee eee eeeeeeeee eeeeeeeeee eee eeeeeee ee 88 °M eee 88 e. Mee eeeeeeee eee eeeeeeee eeee M8M (8 eM) eee eee eeeeeee eee eeeeeeeee eeee MeMMe (8 × 8 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/MeMMe).

8,8-Meeeeeeeeeeeeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

M Meeeeee eeee eeeeeeee eeee e eeeeeee eee eee eeeeeee eeee MeM (8.8 ee, 8.88 eeee, 88 eee%), e-MeMMe (88 ee, 8.8 eeee), eee eee(eeeeeeeeee)eeeeeee (‌8‌; 888 ee, 8.8 eeee). Mee eeeeee eee eeeeeeeee eee eeeeeeee eeee eeeee (8 ×). Meee, ee eeeeeee ‌88‌ (8.8 eeee, 8 eeeee) eee eeeee MMM (8.8 eM) eeee eeeee eee eee eeeeeee eee eeeeeee ee 88 °M eee 88 e. Mee eeeeeeee eee eeeeeeee eeee M8M (8 eM) eee eee eeeeeee eee eeeeeeeee eeee MeMMe (8 × 8 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee MMM (eeeeee eee, eeeeeee/MeMMe).

References