Download PDF
Synthesis 2017; 49(14): 3149-3156
DOI: 10.1055/s-0036-1588800
paper
© Georg Thieme Verlag Stuttgart · New York

Metal- and Acid-Free Methyl Triflate Catalyzed Meyer–Schuster Rearrangement

Authors

  • Lu Yang

    a   Chengdu Institute of Biology, Chinese Academy of Sciences, No. 9 Section 4, Renmin Nan Road, Chengdu 610041, P. R. of China
    b   State Key Laboratory of Geohazard Prevention and Geoenvironment Protection (Chengdu University of Technology), College of Materials, Chemistry & Chemical Engineering, Chengdu University of Technology, 1#, Dongsanlu, Erxianqiao, Chengdu 610059, Sichuan, P. R. of China   Email: qinglezeng@hotmail.com   Email: qlzeng@cdut.edu.cn
    c   University of Chinese Academy of Sciences, Beijing 100049, P. R. of China

  • Qingle Zeng  *

    b   State Key Laboratory of Geohazard Prevention and Geoenvironment Protection (Chengdu University of Technology), College of Materials, Chemistry & Chemical Engineering, Chengdu University of Technology, 1#, Dongsanlu, Erxianqiao, Chengdu 610059, Sichuan, P. R. of China   Email: qinglezeng@hotmail.com   Email: qlzeng@cdut.edu.cn

Supported by: National Natural Science Foundation of China (21372034) Supported by: Department of Science and Technology of Sichuan Province (2016HH0074) Supported by: Education Department of Sichuan Province (16ZA0084) Supported by: Chengdu Science and Technology Bureau (2015-HM01-00362-SF) Supported by: State Key Laboratory of Geohazard Prevention and Geoenvironment Protection Independent Research Project (SKLGP2016Z004)
Further Information

Publication History

Received: 24 January 2017

Accepted after revision: 28 March 2017

Publication Date:
26 April 2017 (online)

   Permissions and Reprints All articles of this category


Graphical Abstract

Abstract

A novel metal- and acid-free preparation of synthetically useful α,β-unsaturated carbonyl compounds from propargyl alcohols has been realized. This Meyer–Schuster rearrangement process is effectively catalyzed by methyl triflate (20 mol%) to prepare a broad scope of conjugated E-enals and E-enones generally in good to excellent yields (up to 90%). This reaction procedure operates under mild conditions (70 °C), in air, with short reaction times (1 h). Moreover, a carbocation intermediate trapped by the solvent 2,2,2-trifluoroethanol was isolated during this transformation.

Key words

Meyer–Schuster rearrangement - methyl triflate - propargyl alcohols - α,β-unsaturated carbonyl compounds - metal-free - acid-free

Supporting Information