Science of Synthesis

Aitken, R. A.; Aitken, K. M., Science of Synthesis, (2010) 41, 197.

Silyl enol ethers, which are a stable alternative to ketone enolates, add to nitroalkenes in the presence of Lewis acid catalysts (‌Scheme 273‌). The reaction is stereoselective when a chiral Lewis acid[‌725‌] or a chiral silyl enol ether with a directing silyl auxiliary[‌726‌] is used.

‌Meeeee 888‌ Meeeeeee ee Meeee Meee Meeeee ee Meeeeeeeeeee[‌888‌,‌888‌]

Meeeeeeeeeee Meeeeeeee

(8M)-8-[(8M)-8-(8-Meeeeeeeeee)-8-eeeeeeeeee]eeeeeeeeeeeee (‌888‌); Meeeeee Meeeeeeee:[‌888‌]

Me e eeeeeeeee (8–88°M), eeeeeeeeee eeeeeee eeee ee [(8M,8M)-8,8-eeeeeeee-8,8-eeeeeeeee-8,8-eeee]eee(eeeeeeeeeeeeeeee) (MMMMMM; 88.88 e, 88 eeee) ee MM8Me8 (888 eM) eee eeeee eeeeeeee eee eeeeeee Me(MMe8)8 (88.8 e, 88.8 eeee). Meee ee eee eeeeeeee eeeeeeeeee eeee eeeeeeeee eee ee eeeeeeeeeee eeeeeeee. Mee eeeeeeee eeeeee ee eeeeeee eee eeeeeee eeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeee (88°M/8.88 Meee) eee 88 e ee eeee eeeeeee ‌888‌ ee e eeeeee, eeeeeeeeeeeeeeee eeeee; eeeee: 88.88 e (88%). Meee eee eeee eeeeeeeee ee eeeeeee (888 eM) eee eeee ee e 8.88 M eeeee eeee.

M 8.88 M eeee ee ‌888‌ (8.888 eeee, 8.88 eM) eeeeeee eeee eeeeeee (88 eM) eee eeeeee ee −88°M (MeMM/eee M8), eee MeMe8 (888 ee, 8.8 eeee) eee eeeee. Mee eeeeeeeeee eeeeeee eeeeeee eee eeeeeee ee eeee ee 88°M eee 8 e, eeeeeeeee ee e eeeee eeeeee-eeeeee eeee ee eeeeeeee eeeeeee ‌888‌ (8.8 eeee). Meee eeee eee eeeeee ee −88°M, eee e eeee ee 8-(8-eeeeeeeeeee)-8-eeeeeeeeeee (‌888‌; 888 ee, 8.8 eeee) ee eeeeeee (8 eM) eee eeeee. Mee eeeeeee eeee (eeeeeee eeee eeeeee ee eeee eee) eee eeeeee ee −88°M, eee 8-(eeeeeeeeeeeeeee)eeeeeeeeeee (‌888‌; 8.88 eM, 8.8 eeee) eee eeeee. Mee eeeeeee eee eeeeeee ee eeee ee −88°M eee 8 e eee eeee eeeeeeee ee −88°M. M eeee ee MeMe8(MeMe)8 [8.8 eeee, eeeeeee eeeeeeee ee eeeeeeee ee MeMe8 (888 ee, 8.88 eeee) ee e eeeeeeeee (8–88°M) eeee ee Me(MeMe)8 (888 ee, 8.88 eeee) ee eeeeeee (88 eM), eeeeeeee ee eeeeeeee ee 88°M eee 8.8 e] eee eeeee eeee e eeeeeee eeee ee <−88°M eeee 88 eee. Mee eeeeeeeee eeeeeee eee eeeeeee ee eeee ee −88°M eee 8.8 e eee eeeeeee ee eeee eeeeeeeeeee (eee eee/eeeeeee) eee 88 e. Me eee eeee eeeeee eeee e eeeeeeeeee eeeeeee eeeeeee eeeeeee ee Me8M (88 eM) eee eee. ee MeMMM8 (88 eM) eee eeeeeeee eeeeeee e eee ee Meeeee. Mee eeeeeee eeeee eee eeeeeeeee eeee Me8M (8×), eee eee eeeeeeee eeeeeeee eeee eeeeee eeee M8M eee eeeee ee 8°M (MeMMM8/MeMM8 8:8), eee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee (eeeee eeee <88°M). Mee eeeeeee eee eeeeeeeee ee MeMM (88 eM), eee MM8M (888 ee, 8.8 eeee) eee eeeee. Mee eeeeeeeee eeee eee eeeeeee ee 88°M eee ee. 88 e, eeeeee eeee eee eeeee (888 eM), eee eeeeeeeee eeee Me8M (8×). Mee eeeeeeee eeeeeeee eeee eeeee (MeMM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeee ee eeeeeeeeeeeeee (eeeeee/Me8M 8:8 ee 8:8) ee eeeeee MMMMMM (88–88% eeeeeeee) eee ‌888‌ ee e eeeeee eeeeeeeeeeee; eeeee: 888 ee (88%); ee 888.8–888°M; [α]Mee −88.8 (e 8.8, MMMe8); 8M MMM (MMMe8, δ): 8.88 (e, 8M, M = 8.8 Me), 8.88 (e, 8M, M = 8.8 Me), 8.88 (ee, 8M, M = 88.8, 8.8 Me), 8.88 (ee, 8M, M = 88.8, 88 Me), 8.88 (ee, 8M, M = 8.8, 88 Me), 8.88–8.88 (e, 8M), 8.88–8.88 (e, 8M), 8.88–8.88 (e, 8M), 8.88–8.88 (e, 8M), 8.88–8.88 (e, 8M).

References