Diastereo- and enantioselective [3 + 3] cycloaddition of spirocyclopropyl oxindoles using both aldonitrones and ketonitrones

Peng-Wei Xu, Jia-Kuan Liu, Lan Shen, Zhong-Yan Cao, Xiao-Li Zhao, Jun Yan () and Jian Zhou ()
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Peng-Wei Xu: East China Normal University
Jia-Kuan Liu: Nanjing University
Lan Shen: Nanjing University
Zhong-Yan Cao: East China Normal University
Xiao-Li Zhao: East China Normal University
Jun Yan: Nanjing University
Jian Zhou: East China Normal University

Nature Communications, 2017, vol. 8, issue 1, 1-8

Abstract: Abstract Optically active spirocyclic compounds play an important role in drug discovery, and new synthetic strategies for the efficient generation of spiro stereocenters are in much demand. Here we report a catalytic enantioselective cycloaddition using spirocyclic donor–acceptor cyclopropanes as a promising approach for the generation of spiro stereocenters. A diastereo- and enantioselective [3 + 3] cycloaddition of spirocyclopropyl oxindoles with both aldonitrones and ketonitrones is developed. The key to reaction development is the activation of spirocyclopropyl oxindoles by a suitable electron-withdrawing N-protecting group. This activation approach offers the promise of a general solution to enable spirocyclopropyl oxindoles as synthons for catalytic enantioselective synthesis of spirocyclic oxindoles featuring a C3 spiro stereocenter, a prominent structural motif in drugs and pharmaceutically active compounds. This protocol also constitutes the catalytic enantioselective reaction using unactivated achiral ketonitrones to construct tetrasubstituted carbon stereocenters.

Date: 2017
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DOI: 10.1038/s41467-017-01451-1

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