Direct Stereodivergent Olefination of Carbonyl Compounds with Sulfur Ylides.
J Am Chem Soc
; 144(27): 12536-12543, 2022 07 13.
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| ID: mdl-35770382
ABSTRACT
The reactivity of phosphorus and sulfur ylides toward carbonyl compounds constitutes a well-known dichotomy that is a common educational device in organic chemistryâthe former gives olefins, while the latter gives epoxides. Herein, we report a stereodivergent carbonyl olefination that challenges this dichotomy, showcasing thiouronium ylides as valuable olefination reagents. With this method, aldehydes are converted to Z-alkenes with high stereoselectivity and broad substrate scope, while N-tosylimines provide a similarly proficient entry to E-alkenes. In-depth computational and experimental studies clarified the mechanistic details of this unusual reactivity.
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