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Asymmetric synthesis of cyclopentanes bearing four contiguous stereocenters via an NHC-catalyzed Michael/Michael/esterification domino reaction.

ABSTRACT: An NHC-catalyzed Michael/Michael/esterification domino reaction via homoenolate/enolate intermediates for the asymmetric synthesis of tetrasubstituted cyclopentanes bearing four contiguous stereocenters is described. A variety of ?,?-unsaturated aldehydes and 2-nitroallylic acetates react well with good domino yields and high stereoselectivities.

SUBMITTER: Shu T

PROVIDER: S-EPMC5315016 | biostudies-literature | 2016 Feb

REPOSITORIES: biostudies-literature

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Asymmetric synthesis of cyclopentanes bearing four contiguous stereocenters via an NHC-catalyzed Michael/Michael/esterification domino reaction.

Shu Tao T Ni Qijian Q Song Xiaoxiao X Zhao Kun K Wu Tianyu T Puttreddy Rakesh R Rissanen Kari K Enders Dieter D

Chemical communications (Cambridge, England) 20160111 12

An NHC-catalyzed Michael/Michael/esterification domino reaction via homoenolate/enolate intermediates for the asymmetric synthesis of tetrasubstituted cyclopentanes bearing four contiguous stereocenters is described. A variety of α,β-unsaturated aldehydes and 2-nitroallylic acetates react well with good domino yields and high stereoselectivities. ...[more]

PMID: 26750327

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