Science of Synthesis

Kaufmann, D. E.; Burmester, C., Science of Synthesis, (2005) 6, 918.

An important synthetic application of propargylboranes is their reaction with carbonyl compounds (‌Scheme 7‌) and analogues. They react with aldehydes, ketones, or imines by a proposed cyclic mechanism to give α-allenic alcohols ‌12‌ or amines in high purity.

Mee eeeeeeee eee eeee eeeeeeeeeee eeeeeee ee eee eeee ee 8-(eeeeeeeeeeeeee)eeee-8-eeee-8-eeeeeeeeeee[8.8.8]eeeeee,[‌8‌–‌8‌] eeeeeeee eeeeeee eeeeeeee ‌88‌ (M8 = MMM) ee eeee eeeeee eee eeeeeeeeeeeeee ee eeeeeeee eeeeeeeeeee eeeeeeee (‌Meeeee 8‌). Mee eeeeeeee eeeee eee eeee eeeeeeee ee eeee eeeeeeeeeeeeeeee. Meeeeeeee eeeeee eeeee eeeeee eeee eeeeeee, eee eeeeeeeee eeeeeeeee eeeee eeeeee eeee eeeeeeee eee eeeeee eeeeeeeeee.[‌8‌] Meee e eeeeeee ee eee eeeeeeee eeeeeeee eee eeeeeeee ee eeee eeeee, eee eeeee eee eeeeeeee eeeeeeeee ee eee eeeeeeeeeee eeeeeee eee eeeeeeeeeee eeeeeee eee eeeeeeeeeee eeee ee eee eeeeee. Mee eeeeeeeeeee eee ee eeeeeeee eeeeeeeeee ee eee eeeeee ee eeeeeeeeeeee eee eeeeeeee eeeeeeeeeee, eeeeeee eeeeeee −88 eee 88°M. Meee eeeeee e eeee eeeeeeeeeee eeeeeeeee eee eeee eeeeeeeeeee.[‌8‌]

‌Meeeee 8‌ Meeeeeee ee Meeeeeeeeeeeeeee eeee Meeeeeee Meeeeeeee[‌8‌,‌8‌,‌8‌]

‌Meeeeeeeeee 8‌

Mee eee ee eeeeeeeee eeeeee 8,8-eeeeeeee-8-eeee-8-eeee-8,8-eeeeeee-8,8,8-eeeeeeeeeeeeeee (‌8‌; ‌Meeeee 8‌) ee eeeeeeeee eeee eeeeeee eeeeeeeee eee eeeeeee eee eeeeeeeeeeeee eeeeeee eeeeeeee ‌88‌ ee eeee eeeeeeee eee eeeeeeeee eeeeeee eeeeee (ee ee 88% ee) (‌Meeeee 8‌).[‌8‌] Meee eeeeeeeeeee eee ee eeeeeeee ee eeeeeeee eee eeeeeeeeeee eeeeee eeeeeeeeee. Meee eeeeeee eee eeeeeee eeee eeee ee eee eeeeeeeee ee e eeeeeeeeee.[‌88‌]

Meeeeeeeeeee eeeeeeeee

(M)-(+)-Meee-8,8-eeee-8-ee [‌88‌, M8 = M8 = M; M8 = (MM8)8Me]; Meeeeee Meeeeeeee:[‌8‌]

M eeee ee eeeeeeeeeeeeeee ‌8‌ [eeeeeeee eeee (8M,8M)-8,8-eeeeeeee-M8,M8-eeeeeeeeeeeee-8,8-eeeeeee (8.88 eeee), MMe8 (8.8 eeee), eee eeeeeeeeeeeeeeeeee (8.88 eeee), ee eeeeeeeee ee Meeeeee ‌8.8.88.8.8‌] eee eeeeee ee −88°M, eee e eeee ee eeeeeee (88.8 ee, 8.88 eeee) ee MM8Me8 (8 eM) eee eeeee eeeeeeee. Meeee eee eeeeeee eee eeeeeee eee 8.8 e, eee eeeeeeee eee eeeeeeee ee −88°M eeee eeeeeee eeeeee eeee (8 eM), eee eee eeeeeee eee eeeeeeeee eeee MM8Me8 (8 eM). Mee eeeeeee eeeee eee eeeeee eeee eeeee, eeeeeeeeeeee, eee eee eeeeeee eee eeeeeeeee ee Me8M/eeeeee (8:8, 88 eM). Meeee eee eeeeeee eee eeeee ee 8°M eee 88 eee, eee eeeeee eee-eeeeeeeeeee eee eeeeeee ee eeeeeeeeee (>88% eeeeeeee), eee eeeeeeee eee eeeeeee eeeeeeeeee eeee e 88% ee MM eeee (88 eM), eee eee eeeeeeeee eeeeeee eeeee eee eeeee (MeMM8). Mee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee); eeeee: 88%.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 88/8e, 888.