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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

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
› Author AffiliationsSupported 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)
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Publication History

Received: 24 January 2017

Accepted after revision: 28 March 2017

Publication Date:
26 April 2017 (online)

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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

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588800.
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