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Aggarwal, V. K.; McGarrigle, E. M.; Shaw, M. A., Science of Synthesis: Stereoselective Synthesis, (2011) 2, 335.
The use of a chiral protecting group on the imine nitrogen can result in control of the configuration of the only stereocenter being formed in the reactions of trimethylsulfonium and trimethylsulfoxonium ylides.[86] Interestingly, trimethylsulfonium and trimethylsulfoxonium ylides, derived from sulfonium salts 45 and 46, respectively, exhibit the opposite diastereoselectivity from one another in this chemistry. More recently, this chemistry has been extended to reactions of semistabilized ylides such as that derived from sulfonium salt 48.[87,88] Chiral tert-butylsulfinyl groups have proven to be the most useful groups for this purpose, although other sulfinyl groups[89,90] and chiral phosphonates[91] have also been employed. Examples, forming 1-(tert-butylsulfinyl)aziridines 47 and 49, are given in Scheme 28.
Meeeee 88 Meeeeeeeeeeee ee Meeeee M-(eeee-Meeeeeeeeeeee)eeeeee[88,88]
M8 | Meee(ee)eeeee Meee | Meeeeeeeee | ee [(8M)-88/(8M)-88] | Meeee (%) | Mee |
---|---|---|---|---|---|
Me | 88 | MMMM, ee, 8 e | 88:88 | 88 | [88] |
Me | 88 | eeeeeee, ee, 8 e | 88:8 | 88 | [88] |
(M)-MM=MMMe | 88 | MMMM, ee, 8 e | 88:88 | 88 | [88] |
M8 | Meee (eee) | Meeeee (eeeee/eee) | ee [(8M)-88/(8M)-88] | Meeee (%) | Mee |
---|---|---|---|---|---|
Me | 88 | 88:88 | 88:8 | 88 | [88] |
8-MeMM8M8 | 88 | 88:88 | 88:8 | 88 | [88] |
8-M8MM8M8 | 88 | 88:88 | 88:8 | 88 | [88] |
e Meeee (eeeee/eee) eeeeee ee eee eeeeeeee eeeeeeeeeeeeeee ee eee M8 eee M8 eeeeeeeeeeee ee eee eeeeeeeee eeee.
Meeeeeeeeeee Meeeeeeee
8-Meeeeeeeeee 8-(eeee-Meeeeeeeeeeee)eeeeeeeeee 88; Meeeeee Meeeeeeee eee eee Meeeeeeeeeeee ee M-Meeeeeeeeeeeee Meeee Meeeeeeeeeeeeeeee Meeeeeeee:[88]
Meeeeeeee MeM (8.88 eeee, 8 eeeee) eee eeeee eeeeeeeeeee ee e eeee ee eeeeeeeeeeeeeeeeee eeeeee (88; 8.88 eeee, 8 eeeee) ee eeeee MMMM (8 eM). Meeee eeeeeeee eee eeee ee ee eee 8 e, eee M-eeeeeeeeeeeee (8.88 eeee, 8 eeeee) ee MMMM (88 eM), eeeee eeeee, eee eeeee. Mee eeeeeee eee eeeeeee ee ee eeeee eee eee eeeeeeee eeeeeeee eee eeeeeeee, eee eeee eeeeee eeee eeeeeee eee eee eeeeeeeee eeee Me8M (8 × 888 eM). Mee eeeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee (888 eM), eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeeeee eeeeeee ee eeeeeeeeeeeee eee eeee eeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee).
8-Meeeeeeeeee 8-(eeee-Meeeeeeeeeeee)eeeeeeeeee 88; Meeeeee Meeeeeeee eee eee Meeeeeeeeeeee ee M-Meeeeeeeeeeeee Meeee Meeeeeeeeeeeeeeeeee Meeeeeeee:[88]
Meeeeeeee MeM (8.88 eeee, 8 eeeee) eee eeeee eeeeeeeeeee ee e eeee ee eeeeeeeeeeeeeeeeeeee eeeeee (88; 8.88 eeee, 8 eeeee) ee eeeee eeeeeee (8 eM). Meeee eeeeeeee eee eeee ee ee eee 8 e, eee M-eeeeeeeeeeeee (8.8 eeee, 8 eeeee) ee eeeeeee (88 eM), eeeee eeeee, eee eeeee. Mee eeeeeee eee eeeeeee ee ee eeeee eee eee eeeeeeee eeeeeeee eee eeeeeeee, eee eeee eeeeee eeee eeeeeee eee eee eeeeeeeee eeee MeMMe (8 × 888 eM). Mee eeeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee (888 eM), eeeee (Me8MM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeeeee eeeeeee ee eeeeeeeeeeeee eeeee eeee ee eeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee).
8-Meeeeeeeeee 8-(eeee-Meeeeeeeeeeee)-8-eeeeeeeeeeeeeee 88; Meeeeee Meeeeeeee eee eee Meeeeeeeeeeee ee M-Meeeeeeeeeeeee Meeee Meeeeeeeeeeeee Meeeee:[88]
M eeee ee 8-eeeeeeeeeeeeeeeeeeeeeeeeee eeeeeee (88; 8.8 eeee) ee eeeee MMM (8 eM) eee eeeeeee ee ee eeeee eeeee. Meeee 88 eee, e eeee ee eee M-(eeee-eeeeeeeeeeeee)eeeee (8 eeee) ee eeeee MMM (8 eM) eee eeeee. Mee eeeeee eeeeeeeeee eee eeee eeeeeee eee e eeeeeee 88 eee. Me eeee eeeee eee e-MeMMe (8.8 eeee, 8.8 eeeee) eee eeeee eeeeeeeeeee ee eee eeeeeee, eeeeeeeee ee e eeeeeeeeeee eeeee eeeeee. Meee eee eeeeeeee eee eeeeeeee (MMM), eee-eeee eeeee (88 eM) eee eeeee eee eee eeeeeeee eeeeeee eee eeeeeee eeeeeee eee 88 eee. Mee eeeeeeeee eeeeee eeeeeee eee eeee eeeeeeee eeeeeee e eee ee Meeeee, eee eee eeeeeeee eee eeeeeeeee eeee Me8M, eeeeee eeee eeeee, eee eeeee (Me8MM8). Mee eeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeeee e eeeee eeeeeee eeeeeeeeee eee eeeeeeeee. Mee eeeeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee.
References
[86] | Meeeíe-Meeee, M. M.; Meeeáeeee, M.; Meeeeeee, M.; Meee, M. M., Meeeeeeeeee: Meeeeeeee, (8888) 8, 8888. |
[87] | Meeeee, M.; Meeeeee, M.; Meeee, M. M.; Meeeeeee, M. M., Mee. Meee., (8888) 8, 8888. |
[88] | Meeeeee, M.; Meeeee, M.; Meeee, M.; Meeeeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[89] | Meeeáeeee, M.; Meeeeeee, M.; Meee, M.; Meeeeee, M.; Áeeeeee, M.; Meeee, M., Mee. Meee., (8888) 8, 8888. |
[90] | Mee, M.; Me, M.; Meee, M.; Me, M.; Meee, M., Meeee. Meeeee., (8888) 88, 8888. |
[91] | Meeeeeeeee, M.; Me, M., Meeeeeeeeee Meee., (8888) 88, 8888. |