Enantioselective Synthesis of (Thiolan-2-yl)diphenylmethanol and Its Application in Asymmetric, Catalytic Sulfur Ylide-Mediated Epoxidation

This work describes an expeditious and efficient preparation of enantiopure (thiolan-2-yl)­diphenylmethanol (2) featuring a double nucleophilic substitution and Shi epoxidation as key steps. One of the applications of its benzyl ether derivative to asymmetric sulfur ylide-mediated epoxidation with u...

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Veröffentlicht in:Journal of organic chemistry 2013-06, Vol.78 (11), p.5788-5793
Hauptverfasser: Wu, Hsin-Yi, Chang, Chih-Wei, Chein, Rong-Jie
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Sprache:eng
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Zusammenfassung:This work describes an expeditious and efficient preparation of enantiopure (thiolan-2-yl)­diphenylmethanol (2) featuring a double nucleophilic substitution and Shi epoxidation as key steps. One of the applications of its benzyl ether derivative to asymmetric sulfur ylide-mediated epoxidation with up to 92% ee (14 examples) was also demonstrated herein.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo400648f