Enantioselective synthesis of (thiolan-2-yl)diphenylmethanol and its application in asymmetric, catalytic sulfur ylide-mediated epoxidation

Hsin-Yi Wu; Chih-Wei Chang; Rong-Jie Chein

doi:10.1021/jo400648f

Enantioselective synthesis of (thiolan-2-yl)diphenylmethanol and its application in asymmetric, catalytic sulfur ylide-mediated epoxidation

J Org Chem. 2013 Jun 7;78(11):5788-93. doi: 10.1021/jo400648f. Epub 2013 May 15.

Authors

Hsin-Yi Wu¹, Chih-Wei Chang, Rong-Jie Chein

Affiliation

¹ Department of Chemistry, National Central University, Taoyuan, Taiwan 32001.

PMID: 23638685
DOI: 10.1021/jo400648f

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzyl Alcohols / chemical synthesis*
Benzyl Alcohols / chemistry
Catalysis
Epoxy Compounds / chemical synthesis*
Epoxy Compounds / chemistry
Molecular Structure
Stereoisomerism
Sulfhydryl Compounds / chemical synthesis
Sulfhydryl Compounds / chemistry*

Substances

(thiolan-2-yl)diphenylmethanol
Benzyl Alcohols
Epoxy Compounds
Sulfhydryl Compounds