Synlett 2020; 31(07): 730-736
DOI: 10.1055/s-0039-1691594
letter
© Georg Thieme Verlag Stuttgart · New York

Beyond the Tebbe Olefination: Direct Transformation of Esters into Ketones or Alkenes

Anna M. Domżalska-Pieczykolan
,

The authors are grateful to Narodowe Centrum Nauki (National Science Centre of Poland) for financial support of the project (research grant PRELUDIUM No. UMO-2017/25/N/ST5/00209 and OPUS No. UMO-2013/11/B/ST5/01188).
Further Information

Publication History

Received: 23 December 2019

Accepted after revision: 24 January 2020

Publication Date:
06 February 2020 (online)


Preview

Abstract

A direct, effective, and operationally simple transformation of esters into ketones or alkenes by the exclusive action of Tebbe’s reagent has been developed. The transformation utilizes the dual character of Tebbe’s reagent as both a methylenation agent and a rearrangement catalyst in the reaction of a wide range of substituted vinyl ethers. The resulting transformation involves sequential methylenation and rearrangement reactions and it offers a high degree of selectivity toward the synthesis of ketones or alkenes. The scope and limitations of the developed methods have been also examined.

Supporting Information