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. 2016 Feb 11;52(12):2609-11.
doi: 10.1039/c5cc09581f. Epub 2016 Jan 11.

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

Tao Shu  1 , Qijian Ni, Xiaoxiao Song, Kun Zhao, Tianyu Wu, Rakesh Puttreddy, Kari Rissanen, Dieter Enders
Affiliations

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

Tao Shu et al. Chem Commun (Camb). .

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 α,β-unsaturated aldehydes and 2-nitroallylic acetates react well with good domino yields and high stereoselectivities.

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Figures

Fig. 1
Fig. 1. Representative natural products and pharmaceuticals bearing a cyclopentane core.
Scheme 1
Scheme 1. Substrate scope. All reactions were performed on a 0.5 mmol scale. The yields of the isolated products are after column chromatography. The diastereomeric ratios were determined by 1H NMR spectroscopy and the e.r. values by HPLC on a chiral stationary phase.
Fig. 2
Fig. 2. Absolute configuration of 3h determined by X-ray structural analysis.
Scheme 2
Scheme 2. Proposed catalytic cycle.
See this image and copyright information in PMC

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