Asymmetric radical carboesterification of dienes

Xiaotao Zhu, Wujun Jian, Meirong Huang, Daliang Li, Yajun Li, Xinhao Zhang and Hongli Bao ()
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Xiaotao Zhu: Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences
Wujun Jian: Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences
Meirong Huang: Peking University Shenzhen Graduate School
Daliang Li: College of Life Sciences, Fujian Normal University
Yajun Li: Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences
Xinhao Zhang: Peking University Shenzhen Graduate School
Hongli Bao: Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences

Nature Communications, 2021, vol. 12, issue 1, 1-9

Abstract: Abstract The straightforward strategy of building a chiral C-O bond directly on a general carbon radical center is challenging and stereocontrol of the reactions of open-chain hydrocarbon radicals remains a largely unsolved problem. Advance in this elementary step will spur the development of asymmetric radical C-O bond construction. Herein, we report a copper-catalyzed regioselective and enantioselective carboesterification of substituted dienes using alkyl diacyl peroxides as the source of both the carbon and oxygen substituents. The participation of external acids in this reaction substantially extends its applicability and leads to structurally diverse allylic ester products. This work represents the advance in the key elementary reaction of intermolecular enantioselective construction of C-O bond on open-chain hydrocarbon radicals and may lead to the discovery of other asymmetric radical reactions.

Date: 2021
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DOI: 10.1038/s41467-021-26843-2

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