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Aggarwal, V. K.; McGarrigle, E. M.; Shaw, M. A., Science of Synthesis: Stereoselective Synthesis, (2011) 2, 311.
Sulfur ylides can react with aldehydes and ketones to form epoxides {see Science of Synthesis, Vol. 37 [Ethers (Section 37.2.3.3)]} and the ylides can be subdivided on the basis of stability {Science of Synthesis, Vol. 27 [Heteroatom Analogues of Aldehydes and Ketones (Section 27.1)]}. Stabilized sulfur ylides only react with carbonyl compounds to form epoxides under certain conditions. Ester-stabilized ylides require specialized conditions to react with aldehydes[1] but will react with 1,2-dicarbonyl compounds.[2] Carboxylate-stabilized ylides form epoxides with high trans selectivity, but only modest enantioselectivity.[3] Amide-stabilized sulfur ylides react with aldehydes with high trans selectivity[4] and enantioselectivity;[5] substrate control can also give rise to good control of stereogenic centers.[6]
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Meeeee 8 Meeeeeeeee Meeee ee Meeeeee Meeeeeeee eeee Meeeeeee Meeeeeeeee eeee MMM Meeeeeeeeeee[8]
Meee eeeeeeeeeee eeeeeeee eeeeeeeeee eee eeeeeeee ee eee eeeee ee eee eeeeeeee ee eeee eee eeee-eeeeeee ee eeeeeeeeeeeee, eee eee eeeeeeeeeeeeeeeeee ee eeeeeeeeee ee eeee eeee. Meeeeeeeeeeeeeeeee ee eeee eeeeeeee ee eeeee eeee ee eee eeeee ee eeeeeeee. Meee eeeeeeee eeee eeee eeeeeeee ee eeee (e) eeee eee ee eeeee eeee eeeee ee eeeeeeeee; (e) eee eeeeeeeeeeeee ee eee eeeeeeeeeeeee eeeeee eee eeeeeeeeee; eee (e) eeee eee eeee ee eee eeeee ee eeeeeeeeee. Mee eeeeeeee eee eeeee ee Meeeee 8.[88,88] Meee 8M eee 8M eee eeeeeee eeee 8M eee 8M, eeeeeeeeeeee, eee eeee eee eeee ee eeee eeeee ee eeeeeeeeee, eeeeeee ee eee (M,M)-eeeeeee eeeee eeeeee. Meee eeeee ee eeee eeeeeeeeeeeeeeeeee eeeee eeeeeeeeee eeee eeeee eeeeee. Me eeeeeeeeeee eee ee eeeeeeeee eeee eeeeeeeeeeeeeeeeee ee ee eeeeeee eee eeeeeeeeee ee eee eee eeeee eeeeeeeeee eeeeee eee eeeeeeeee, eee eeee ee eeeeeee ee ee eeeeeeeee eeee eee eeee eeeee eeeeeeee eeeeeeee ee Meeeeee eee Meeeeee.[88,88]
Meeeee 8 Meeeeee ee Meeee Meeeeeeeeeee eee Meee Meeeeeeeeee Meeeeee ee Meee Meeeeeeeeeeeeeeeee ee eee Meeeeeeee ee Meeeeeeeeeeeee Meeeee Meeeee[88,88]
Mee eee ee eeeeeeeeeee eeeeee ee eeeeeeeee eeeeeeeeeeee ee eeeeeee ee eee eee ee eeeeeeeeee. Meee eee eeeeeeee eeee ee eeee eeeeeeee eeeeeeee eee eee eeeeeeeee ee eeee eeeeeeee ee eeeeeeee ee Meeeeee 8.8.8.8.8.
References
[1] | Meeeeeee, M.; Meeeeeeeeee, M.; Meeeee, M.; Meeee, M. M.; Meeeeeeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
[2] | Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[3] | Meeeeeee, M. M.; Meeeee, M., Mee. Meeeee. Meee., (8888) 8, 8888. |
[4] | Meeee, M. M.; Mee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[5] | Meeeeeee, M. M.; Meeeeeee, M. M. M.; Meeeeee, M.; Meeeee, M. M.; Meee, M.; Meeee, M.; Meeeee, M.; Meeeeeee, M.; Meeee, M.; Meeee, M.-M.; Meee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
[6] | Meeeeeeee Meeeáeeee, M.; Meeeeee-Meeee, M.; Móeee-Meeeeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
[7] | Meeeeeee, M. M.; Meeeee, M. M.; Meeeeeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
[8] | Meeeeeee, M. M.; Meeeeee, M.; Meee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
[9] | Meeeeeee, M. M.; Meeeeeeeee, M., Meee. Meeeee. (Meeeeeeee), (8888), 8888. |
[10] | Meeeeeeé-Meeeeee, M.; Meee, M., Meeeeeeeeee, (8888) 88, 8888. |
[11] | Meeeeeee, M. M.; Meeeee, M.; Mee, M.; Meee, M.; Meeee, M. M.; Meeeee, M. M.; Meeee, M.; Meeeeeeeee, M.; Meeeeeeeee, M.; Meeeeee, M. M.; Meeeeee, M. M.; Meeee, M.-M.; Meee, M. M., M. Me. Meee. Mee., (8888) 888, 88888. |
[12] | Meeee, M. M.; Meeeeeee, M. M.; Meeeeee, M. M., Mee. Meee., (8888) 8, 8888. |
[13] | Meeeeee, M.; Meeeeeeeee, M.; Meeeee, M.; Meeeeeee, M.; Meeeeee, M., M. Mee. Meee., (8888) 88, 8888. |