Organocatalytic Enantioselective Synthesis of 1,4-Dioxanes and Other Oxa-Heterocycles by Oxetane Desymmetrization

Wen Yang; Jianwei Sun

doi:10.1002/anie.201509888

Organocatalytic Enantioselective Synthesis of 1,4-Dioxanes and Other Oxa-Heterocycles by Oxetane Desymmetrization

Angew Chem Int Ed Engl. 2016 Jan 26;55(5):1868-71. doi: 10.1002/anie.201509888. Epub 2015 Dec 21.

Authors

Wen Yang¹, Jianwei Sun²

Affiliations

¹ Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China.
² Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China. sunjw@ust.hk.

PMID: 26689744
DOI: 10.1002/anie.201509888

Abstract

A new asymmetric synthesis of chiral 1,4-dioxanes and other oxa-heterocycles has been developed by means of organocatalytic enantioselective desymmetrization of oxetanes. This mild process proceeds with exceedingly high efficiency and enantioselectivity to establish the quaternary stereocenters. This method complements the existing, yet limited, strategies for the synthesis of these oxa-heterocycles.

Keywords: asymmetric catalysis; cyclizations; heterocycles; hydrogen bonds; organocatalysis.

Publication types

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