Dearomative Mislow-Braverman-Evans Rearrangement of Aryl Sulfoxides.

ABSTRACT: The Mislow-Braverman-Evans rearrangement, the reversible [2,3]-sigmatropic rearrangement of allylic sulfoxides to allylic sulfenate esters, finds widespread applications in organic synthesis and medicinal chemistry. However, the products of this powerful strategy have primarily been limited to derivatives of allylic alcohols. In contrast, access to structurally similar benzylic alcohols has not yet been established. Described herein is an unprecedented dearomative Mislow-Braverman-Evans rearrangement of aryl sulfoxides to afford benzylic alcohols. A variety of heteroaryl sulfoxides as well as α-naphthyl sulfoxides could be tolerated, and a diverse range of primary, secondary, and tertiary alcohols possessing either alkyl or aryl substituents can be prepared by our protocol with broad funct

SUBMITTER: Zhang X 

PROVIDER: S-EPMC11863165 | biostudies-literature | 2025 Feb

REPOSITORIES: biostudies-literature