Literature DB >> 28194849

Enantioselective Aza-Ene-type Reactions of Enamides with Gold Carbenes Generated from α-Diazoesters.

Feng Zhao1, Nan Li1, Tao Zhang1, Zhi-Yong Han1, Shi-Wei Luo1, Liu-Zhu Gong1,2.   

Abstract

Carbophilic gold carbenes generated from the decomposition of α-diazoesters show high reactivity towards enamides, leading to an unprecedented aza-ene-type reaction. The presence of 0.1 mol % of a chiral Brønsted acid co-catalyst is sufficient to give synthetically relevant γ-keto esters in excellent yields and selectivities (up to 99 % yield, 97 % ee).
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Brønsted acids; asymmetric protonation; aza-ene reactions; gold carbenes; relay catalysis

Year:  2017        PMID: 28194849     DOI: 10.1002/anie.201612208

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  1 in total

1.  Gold-catalyzed stereoselective dearomatization/metal-free aerobic oxidation: access to 3-substituted indolines/oxindoles.

Authors:  Kai Liu; Guangyang Xu; Jiangtao Sun
Journal:  Chem Sci       Date:  2017-11-06       Impact factor: 9.825

  1 in total

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