Science of Synthesis

MacMillan, D. W. C.; Watson, A. J. B., Science of Synthesis: Asymmetric Organocatalysis, (2012) 1, 382.

Enantioenriched sulfur compounds have found synthetic significance in a number of areas. Additionally, the ease with which sulfur nucleophiles participate in 1,4-addition processes with α,β-unsaturated carbonyl compounds has led to considerable exploration by the synthetic community.[‌179‌] Such processes are now readily achieved under a variety of conditions and asymmetric methods have also been extensively developed.

Meeeeee eeeeeeeee eee eeee eeeeeeeee ee eeeeeee e eeeeeeeeee eeeeee eee eee eeeeeeeeeeeeeeee eeeeeeeee ee eeeeee eeeeee eeeeeeeee.[‌888‌–‌888‌] Meeeeee, eeeee eeee eeeeeeeee eee eeeeeee eee ee eeeeeeee, eee eeeeeeeee eeeee ee eeeeeeeeee eeee eeee eeeeee eeeeeeeeeeeee eeeeee eeeee eeee ee eeeee eeeeeeeeeeee eeeee eeeeeeeee ee eee eeeeeeee eeeeeeee. Meeeeeeeeeee, eee eeeeeeeeee ee eee eeeee eeeeeeeee eee eeeeeeeee.

Mee eeeeeeeeeeeeeee eeeeeeeeee eeeeeee eeeeee ee eee eeeeeeee eeeeeeeeee eeeee eeeeeeeeeee ee eee eeeeeeee eeeeeee, eee eeeeeeee eeeeee eee eeeeeeeeeeeeeeeeeeee eeee eee eeeeeeeee eeee ee eeeeeeeee (‌Meeee 88‌). Meeeeeee eeeeeeeeee eee eeeeeee eeeeeeee ee eee eeeeeeeeeeeee eeeeeeee, eeeeeeee eeeee eeeeeeeee eeee eeeeee eeeeeeeeeee, eeeeeee eeeeee-eeeee eeeeeeee eee eeeeeeee eeeeeeee.

‌Meeee 88‌ Meeeeeeeeeeeeeee 8,8-Meeeeeee ee Meeeee Meeeeeeeeeee[‌888‌–‌888‌]

Meeee	Meeeeeee Meeeeeeee		Meeeee	Meeeeeeeee	Meeeeee	ee (%)	Meeee (%)	Mee
	Meeeeeeee	Meeee
8		e-MeMM	8.8:8	‌88‌ (8.8 eeeee), MeMM (8.8 eeeee), eeeeeee, −88 °M		88e	88e	[‌888‌]
8		MeMM	8.8:8	‌88‌ (8.8 eeeee), MeMM (8.8 eeeee), eeeeeee, −88 °M		88e	88e	[‌888‌]
8		MeM8MMM8MM	8.8:8	‌88‌ (8.8 eeeee), MeMM (8.8 eeeee), eeeeeee, −88 °M		88e	88e	[‌888‌]
8		MeMM	8:8.8	‌88‌ (8.88 eeeee), (M)-MeeM(Me)MM8MM8M (8.8 eeeee), eeeeeee (8.88 M), −88 °M		88	88	[‌888‌]
8		MeMM	8:8.8	‌88‌ (8.8 eeeee), (M)-MeeM(Me)MM8MM8M (8.8 eeeee), eeeeeee (8.88 M), −88 °M		88	88	[‌888‌]
8e		e-MeMM	8:8.8	‌88‌ (8.8 eeeee), (M)-MeeM(Me)MM8MM8M (8.8 eeeee), eeeeeee (8.88 M), ee		88	88	[‌888‌]
8		MeMM	8:8.8	‌88‌ (8.8 eeeee), MMMM (8.8 eeeee), MM8Me8 (8.8 M), 88 °M		88	88	[‌888‌]

e Meeee (eeeeeeeee/eeeee).

e Me eeeeeeeeeeeee eeeeeee.

Meeeeeeeeeee Meeeeeeee

(M)-8-(eeee-Meeeeeeeeeeee)-8-(8-eeeeeeeeeeee)eeeeee-8-ee (‌Meeee 88‌, Meeee 8); Meeeeee Meeeeeeee:[‌888‌]

Me e eeeeeee ee (M)-8-{eee[8,8-eee(eeeeeeeeeeeeeee)eeeeee](eeeeeeeeeeeeeee)eeeeee}eeeeeeeeeee (‌88‌; 88.8 ee, 8.888 eeee, 8.8 eeeee), MeMM (8.8 ee, 8.888 eeee, 8.8 eeeee), eee (M)-8-(8-eeeeeeeeeeee)eeeeeeee (88.8 ee, 8.88 eeee, 8.8 eeeee) ee eeeeeee (eeeeee eee eeeeeeee) ee −88 °M eee eeeee e-MeMM (88.8 ee, 8.88 eeee, 8 eeeee). Mee eeeeeeeee eeeeeee eee eeeeeee ee −88 °M eee 88 e eeeeee eeeee eeeeeee eeee MeMM (8 eM) eee MeMM8 (88.8 ee, 8.8 eeee, 8 eeeee) ee 8 °M. Mee eeeeeeeee eeeeeee eee eeeeeee ee 8 °M eee 88 eee eeeeee eeeee eeeeeeee eeee eee. ee MM8Me eee eeeeee eeee 8 M ee MeMM eee eeeee (eeeeeee eee eeeeeeee). Mee eeeeeee eeeee eee eeeeeeeee, eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee e eeeeeee, eeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeeee eee eeeeeeee); eeeee: 88.8 ee (88%); 88% ee. Mee eeeeeeeeeeee eeeeee eee eeeeeeeeee ee MMMM eeeeeeee [MM eeeeee, eMeMM/eeeeee 8:88; eM (eeeee) = 88.8 eee, eM (eeeee) = 88.8 eee].

(M)-8-(Meeeeeeeeeeeee)-8-(8-eeeeeee)eeeee-8-eee (‌Meeee 88‌, Meeee 8); Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee (8M)-(8-eeeeeeeeeeeeeeee-8-ee)(8-eeeeeeeeeeeeeee-8-ee)eeeeeeeeeee (‌88‌; 8.8 ee, 8.88 eeee, 8.88 eeeee) eee e-M-(eeee-eeeeeeeeeeeeee)eeeeeeeeeeeee (88.8 ee, 8.88 eeee, 8.8 eeeee) ee eeeeeee (8.8 eM) eee eeeeeee ee ee eee 88 eee. Mee eeeeeee eee eeee eeeeeee eeee (M)-8-(8-eeeeeee)eee-8-ee-8-eee (88.8 ee, 8.8 eeee, 8 eeeee) eee eeeeee ee −88 °M. Mee eeeeeee eee eeeeeee ee −88 °M eee 88 eee eeeeee MeMM (88.8 ee, 8.88 eeee, 8.8 eeeee) eee eeeee. Mee eeeeeeeee eeeeeee eee eeeeeee ee −88 °M eee 88 e eeeeee eeeee eeeeeee eeee eeeeee (8 eM) eee eeeeeeee eeeeeee e eee ee eeeeee, eeeeeee eeee Me8M/eeeeee (8:8). Mee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee e eeeeeee, eeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (Me8M/eeeeee 88:88); eeeee: 88.8 ee (88%); 88% ee. Mee eeeeeeeeeeee eeeeee eee eeeeeeeeee ee MMMM eeeeeeee [MM-M eeeeee, eMeMM/eeeeee 8:8, 888/888 ee, 8.88 eM · eee−8; eM (eeeee) = 8.8 eee, eM (eeeee) = 8.8 eee].

References