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手性自由基环丙腈化反应通过双光氧化还原和铜催化肟酯。

Enantioselective Radical Ring-Opening Cyanation of Oxime Esters by Dual Photoredox and Copper Catalysis.

机构信息

CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticide & Chemical Biology Ministry of Education, College of Chemistry , Central China Normal University , 152 Luoyu Road , Wuhan , Hubei 430079 , China.

State Key Laboratory of Applied Organic Chemistry , Lanzhou University , Lanzhou 730000 , China.

出版信息

Org Lett. 2019 Dec 6;21(23):9763-9768. doi: 10.1021/acs.orglett.9b03970. Epub 2019 Nov 20.

DOI:10.1021/acs.orglett.9b03970
PMID:31746212
Abstract

Catalytic enantioselective chemical reactions involving highly reactive radical species remain largely unexplored. We report herein for the first time a novel enantioselective radical ring-opening cyanation of redox-active oxime esters by dual photoreodox and copper catalysis. This mild protocol shows good functional group tolerance and broad substrate scope, producing a wide range of optically active alkyl dinitriles with high yields and excellent enantioselectivities, which are difficult to access traditionally.

摘要

涉及高反应性自由基物种的催化对映选择性化学反应在很大程度上仍未得到探索。本文首次报道了双光氧化还原和铜催化下氧化肟酯的新型对映选择性自由基开环氰化反应。该温和的反应条件具有良好的官能团耐受性和广泛的底物范围,能够以高产率和优异的对映选择性得到广泛的手性烷基二腈,这在传统方法中很难实现。

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