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DOI: 10.1055/sos-SD-202-00130

Aggarwal, V. K.; McGarrigle, E. M.; Shaw, M. A.Science of Synthesis: Stereoselective Synthesis, (20112311.

Sulfur ylides can react with aldehydes and ketones to form epoxides {see Science of Synthesis, Vol.37 [Ethers (Section]} 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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