Science of Synthesis

Schobert, R.; Gordon, G. J., Science of Synthesis, (2004) 27, 1023.

Three approaches are considered in this section: (1) E-selective alkenation with unstabilized β-oxidophosphonium ylides (Wittig–Schlosser reaction); (2) the SCOOPY procedure (α-substitution plus carbonyl olefination via β-oxidophosphorus ylides, also known as the three-dimensional Wittig alkenation); and (3) Z-selective alkenation with methoxymethoxy-armed moderated ylides. All normally provide alkenes with high degrees of stereoselectivity, but the configuration of the product may vary from one procedure to another.

Meeee eee M-eeeeeeeee eeeeeeeeee ee eeeeeeeee ee eeeeeeeeeeee eeeeee ee eeeeee eeeeeeee eeeee eeee-eeee eee-eeeeeeeeeee eeeeeeeeee (eee Meeeeee ‌88.88.8.8.8.8‌), eee eeeeeeeeeeeee M-eeeeeeeeee eeee eeee eeeeeeee eeeeee eee eeeeeeeee eeeee eee eeeeee ee eee ee-eeeeee Meeeee–Meeeeeeee eeeeeeee ee 8888.[‌888‌,‌888‌] Me eeee eeeeeeeee eee eeeeeeeeeeee eeeee ee eeeeeeee eeee eee eeee eee e eeeeeee eeee (eeeeeeeeeeeee ee eeeeeeeeeeee). Meee ee ee eeeeeee eeee eee eeeeeeee eeeeeeee, eee eee eeeeeeeee eeeeeee eeeeeeeeee eee eeeeeeeeeeee eeeeeee- eee eeeee-eeeeeeee ‌88‌ ee eeeeeeeeeeee/eeeeeeeee ee eeeeee e eeeeee eeeeeeeeee ee eee eeee eeeeeee eeee ee −88°M ee eeee eeeeeeeeeeeee eee eeeeeeeee eeeee-eeeeeee ‌88‌. Mee eeeeeeeeeeeee ee eeee eeeeeeee eeee e eeeeeee eeee ee eeee-eeeee eeeeeee eeee eeeeeeeeeee eeeeeeeeeee eee eeeee-(M)-eeeeeeeeee eeeeeeee eeeeeee, eeeee eeeeeeeee ee eeee eee eeeeeeeeeeeee M-eeeeee ‌88‌ eeeeee eeee eeeeeee ee eeee eeeeeeeee eeee eeee-eeeeeeeee eeeeeeee (‌Meeeee 88‌). M/M Meeeee eeeeeee eeee 88:8 eee eeeeeeeee eeeeeeee eeee eeeeeeeee, eeeeeee eeeeeee eeee eeeeeeee eeeee eeeeeeeeeeeee (ee. 88:88).[‌888‌] Mee eeeeeeee eee ee eeeeeeeee eeee eeeeeee-eeeee eeeeee (eee Meeeeee ‌88.88.8.8.8.8‌).

‌Meeeee 88‌ Meeeee–Meeeeeeee M-Meeeeeeeee eee β-Meeeeeeeeeeeeeee Meeeee[‌888‌]

‌Meeeeeeeeee 88‌

e Meeeeeee eee eeeeeeee ee MM.

e Meeeeeeeeeee (MeMMMe) ee eeee ee eee eeeeeeee eeeeeeeee eeeeee eeee ee eeeeeeee (M8MMM).

eeeee-β-Meeeeeeeeeeeeeee eeeeee ‌88‌ eee eeee ee eeeeeeeeeee ee eeeeeeeeeeeee, eeeee eeee eee eeeeee, eeeeee eeee ee eeeeeeeeeeeeee eeeeeee ‌888‌ (‌Meeeee 88‌) eeee eee eeeeeeeeeeee eeeeeee ee eee eeeeeeee eeeeee α-eeeeee eee eeeeeeee eeeeeeeeee eee ee eee eeeeeeee eeeeeeee eeeeeeeeeee (M8). Meee, eee eeeee eeeeeee ee eeeee ee eee “eeeee-eeeeeeeeeee Meeeee eeeeeeee” ee ee eee “α-eeeeeeeeeeee eeee eeeeeeee eeeeeeeeeee eee β-eeeeeeeeeeeeeee eeeeee (MMMMMM)” eeeeeeeee.[‌8‌,‌888‌,‌888‌] Meeee MMMMMM eeeeeeeee eeeeeee eeeeeeeeeee eeee eeeeeeeee eeeeeeee,[‌888‌] eeeeeeeeeee eeee eeeeeeeeeee,[‌888‌] eeeeeeeeeee eeee eeeeeee,[‌888‌] eeeeeeeeeeee eeee eeeeeeeeee eeeeeeee,[‌888‌] eeeeeeeeeeee eeee eeeeeeeeeee eeeeeeeeee,[‌888‌] eee, eeeeeeee eee eeee eeeeeeeee, eeeeeeeeeeeeeeeeee eeee eeeeeeeeeeee eeeeeeee eeeeeeeeeeeeee M-eeeeeee eeeeeeee.[‌888‌,‌888‌] Mee eeee eeeeeeee eeeeeee eeeeeee ee eeeeeeeee eeee ee eee eeeeeeee eeee eee eeeeeeee eeeeeeee eeeeeeeee eeeeeeeeee ee eee eeeeeeee eeeeee eee eee eeeeeeee ee eee eee eeeeeeeee.[‌888‌] Meee eeeeeeeeeeeeeeeeeee eee eeeeeeee, eeeeeeee eeee ee eeeeeeeeeeee ee eeeee eeee. Meee eeeeeeeee eeeee eeee eeeeeeeeeeee eee eeee, eeeeeeeeee eee eeeeeeee eeee eee eeeeee eeeeeeee ee eeeeeeeeee ee e eeeeeeeee eeeee.

‌Meeeee 88‌ Meeeeeeeeeeeee Meeeeee ee eee MMMMMM Meeeeeeee[‌888‌,‌888‌–‌888‌]

‌Meeeeeeeeee 88‌

M8	M8	M	MMe	Meeee (M/M)	Meeee (%) ee ‌888‌	Mee
M	Me	M	MMe	88:88	88	[‌888‌]
Me	Me	Me	MeM	8:88	88	[‌888‌]
Me	Me	M	MMeM8	88:8	88	[‌888‌]
Me	Me	M	MMeM8	88:8	88	[‌888‌]
Me	Me	Me	MeMMe8	88:8	88	[‌888‌]
Me	Me	Me	Me8	88:88	88	[‌888‌]
Me	(MM8)8Me	MM8MM	MMMM	88:8	88	[‌888‌]
Me	Me	MM8MM	MMMM	88:8	88e	[‌888‌]
Me		MM8MM	MMMM	–e	–e	[‌888‌]

e Meee eeeee: 88% ee eee eeeeeeeeeeeee 8-eeeeeee-8-eeeeee-8-eeeeeeeeee-8-eee.

e Mee eeeeeee eeeee eee eeeeeeee ee ee “M eeeeeeeeeeeeee” eee “eeeeeeeee” eeeeeee eeeeeee eeeeeeeeeeeee.

Meeeeeeee (ee eeeeeeeeeeeeee) eeeeeeeeeeeeeeeeeee eeeeee eee eeeeeeeee eee eeeeee eee M/M eeeeeeeeeeeee ee eee eeeeeeeeee ee eeeeeeeee eee eeeeeeeeeee eeeeeeeee. Meeeeee, eee eeeeeeeeeeee ee 8-eeeeeeeeeeeeee eeee eeeeee eeee eee eeeeee eeeeeeeeeeee ee eee eeeeeeeeee eeee eeeeeeeeeeee eeeeeeeee eee M eeeeeeeeeee ee eee eeeeeee eeeeeee ‌888‌ (eee ‌Meeeee 88‌), eeeeeee ee eeeeee eeee eee eeee eeeeeeeeeeee eeeeeeeeeee ee e eeeeeeeee eeeee.[‌888‌] Mee eeeeee eeeee eeee eee e eeee eeeee ee eeeeeeeee eee eeee(8-eeeeeeeeeeeeeeeeeeee)eeeeeeeeeeee, eeee eeeeeee,[‌888‌] eeee,[‌888‌] α-eeee,[‌888‌] eee α-eeeeeee[‌888‌] eeeeeeeeeeee ee eee eeeeee eeeeee eeee, eeeee eee eeeeeee eeeeeeeeee eeee eeee(8-eeeeeeeeeeeeeeeeeeee)eeeeeeeee[‌888‌] eee eee eeeeeeeeee eeeeeeeeeee eeeee. Mee ee eeeeee eeeeeeeeee, eeeeee eee ee eeee eeeee eeee eeeeeeee. Meeeeeee M eeeeeeeeeee eee eeee eeee eeeeeeee eee eeeeeeeeeeee eeeeeee 8-eeeeeee eeeeeeee ee eee eeeeeeeeee eeee.[‌888‌]

‌Meeeee 88‌ M-Meeeeeeee Meeeeeeeeee eeee Meee(8-eeeeeeeeeeeeeeeeeeee)eeeeeeeeeeee[‌888‌,‌888‌,‌888‌]

‌Meeeeeeeeee 88‌

e Meeeee ee eee eeeee 88–88%.

Meeeeeeeeeee Meeeeeeee

Meeeeee ‌88‌ ee eee Meeeee–Meeeeeeee M-Meeeeeeeee Meeeeeee; Meeeeee Meeeeeeee:[‌888‌]

M eeee ee eeeeeeeeee ee eee eeeeeeeeeee eeee (88 eeee) ee MMM (88 eM) eee Me8M (88 eM) eee eeeeeee eeee MeMe (88 eeee) ee Me8M eee eeeeeee eeeee e eeeeeeee Meeeee eeee eeeeeeeee eeeeeeee eeeeeeeeeee ee MeMe (ee. 88 eee). Mee eeee eee eeeeee ee −88°M eee ee eeeeeeee (88 eeee) ee Me8M (88 eM) eee eeeee ee eeee. Meeeee 8 eee eee eeeeeeeeee eeeeeee eeee, eeeee eee eeee eeeeeee −88°M eee −88°M, eeeeeeeeeee, eee eee eeeeeeeeeeee eeeeeee eeee eeeeeee eeeeeeeeee ee MeMe (88 eeee) ee Me8M ee −88°M. Meee eeeeeeeeeeeee eee eeeeeeee (Meeeee eeee), MMe ee Me8M (88 eeee) eee e-MeMM eeeeeee eeee e-MeMM (88 eeee; 8:8) eeee eeeee ee eeeeeeeee. Mee eeeeeee eee eeeeee ee ee, eeeeeee eee eeeeeee 8 e, eee eeeeeee eeeeeeeeeee ee eeeeee e eeeee eeeeeeeeeee eeeeee. Meee eee eeeeeeeee, eeeeee eeee M8M, eeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eeeeee eee eeeeeeee ee eeeeeeeeeeee ee eeeeee eeeeeeeeeeeeee.

(M)-8-Meeeeee-8-eeeeeeeee-8-eee [‌888‌, M8 = Me; M8 = (MM8)8Me; M = MM8MM]; Meeeeee Meeeeeeee:[‌888‌]

(Meeeeeeeee)eeeeeeeeeeeeeeeeeeee (88.8 e, 88 eeee), eeeeeee eeeeeeee eeee (eeeee)eeeeeeeeeeeeeeeeeeee eeeeeee eee MeMe ee e eeeeeee ee MMM (888 eM) eee eeeeee (88 eM), eee eeeeee ee −88°M eee eeeeeee ee eeee eeee eeeeeee (88 eeee), eeeeeeeee eee eee eeeee ee eee eeeeeee eeeeeeee eeeeeeeeeeeeeee. Meeeeee eeeeeeeeee ee MeMe (88 eeee) eee eeeee ee eeee eeeeeeeeeee eee eee eeeeeee eee eeee eeeeeee ee eeee ee 8°M eee eeeeeee eee 88 eee. Meeeeeeee MMMM (88 eeee) [eeeeeeee ee eeeeeeeeee e eeeeeee ee eeeeeeeeeeeeeeee (8 e), MMM (888 eM), eee e eee eeeee ee MM8•MMe8 eeee e Meeeeee eeee eeee ee −88°M] eee eeeee ee e 8.8 M eeee ee MMM (88 eM) eee eee eeeeeeeee eeeeeeeee eeeeeeeeee eee eeeeeee eee 88 e ee ee. M8M (88 eM) eee eeeee ee eee eeeeeee eee eeeeeeee eee eeeeeeeee eee eeeeeee 8 e. Mee eeeeeeeee eeeeeeeeee eee eeeeeeeeeeee ee eeeeeeeeeee (ee. 888 eM ee eeeeeee eee eeeeeee), eeeeeee eeee M8M (888 eM), eee eeeeeee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeee eeeeee eeee eeeeeeeee, eeeee, eee eeeeeeeeeeee ee e eeeeee eeeeeeeeee. Mee eeeee eeeeeee eeee eeeeeeee eee eeeeeeee ee eeeeeeeeeeee; eeeee: 8.8 e (88%); ee 888–888°M/88 Meee; (M/M) 88.8:8.8 (ee MM, 88% Meeeeeee eeeeee, 8 e, 888°M).

(M)-8-Meeeee-8-eeeeeeeeeee-8,8-eeeee (‌888‌, M8 = MM=MMe8; M8 = Me); Meeeeee Meeeeeeee:[‌888‌]

8-Meeee-8-eeeeeeeee-8-eee (eeeeee eeeeeee; 88.8 e, 88.8 eM, 8.88 eee) eee eeee(8-eeeeeeeeeeeeeeeeeeee)eeeeeeeee[‌888‌] (88.8 e, 8.88 eee) eeee eeeeeeeee ee eeeeeee (888 eM) eee eeeeee ee 88°M eee 8 e. Mee eeeeeee eee eeeeee ee ee eee eee eeee eeeeeeeee eeeeeee eeeeeeeeeee ee 8-eeeeee-8-eeeeeee[eeee(8-eeeeeeeeeeeeeeeeeeee)]eeeeeeeeeee eeeeeee eee eeeeeeeee ee eeeeeeeeee, eeeeee eeee Me8M, eee eeeee eeeee eeeeeee eeeeeeee; eeeee: 88.8 e (88%); ee 888–888°M.

M eeeeeeeeee ee MeMM8 (8.8 e, 88.8 eeee), e-MeMM (8.8 e, 8.8 eeee), eee 8-eeeeee-8-eeeeeee[eeee(8-eeeeeeeeeeeeeeeeeeee)]eeeeeeeeeee eeeeeee (88.8 e, 88.8 eeee) ee MMM (888 eM) eee eeeeeee eeeeeeeeee eee 8 e ee 88°M. Mee eeeeeee eee eeeeee ee −888°M, eee MeMMM (88.8 eM, 8.8 e, 88.8 eeee) eee eeeee. Meeee eeeeeeee eee 8 e ee −888°M, eee eeeeeee eee eeeeee eeee M8M (88 eM) eee eeeeeeeee eeee eeeeee (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee (88 eM), eeeee, eee eeeeeeeeeeee. Meeeeeeeeeee eeee e eeeeeeeee eeeeee; eeeee: 8.8 e (88%); ee 88–88°M/8 Meee; (M/M) 88:8 (ee MM, 8% MM-M, 8 e, 888°M).

References