Organocatalytic synthesis of multiple substituted b[4.4.0]decalin system

Shaik Anwar; Hui Ju Chang; Kwunmin Chen

doi:10.1021/ol200424x

Organocatalytic synthesis of multiple substituted b[4.4.0]decalin system

Shaik Anwar, Hui Ju Chang, Kwunmin Chen

Department of Chemistry

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38 Citations (Scopus)

Abstract

Chemical equations presented. An efficient and unprecedented organocatalytic reaction of γ-nitroketones with α,β-unsaturated aldehydes to give polyfunctionalized [4.4.0] bicyclic skeletons was developed. The diphenylprolinol silyl ether mediated nitro-Michael/Aldol reaction afforded the hexa-substituted decalin carboaldehydes with excellent diastereo- and enantioselectivity (up to >99:1 dr and >99% ee) via a formal [4 + 2] carbocyclization process.

Original language	English
Pages (from-to)	2200-2203
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	9
DOIs	https://doi.org/10.1021/ol200424x
Publication status	Published - 2011 May 6

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ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Cite this

Anwar, S., Chang, H. J., & Chen, K. (2011). Organocatalytic synthesis of multiple substituted b[4.4.0]decalin system. Organic Letters, 13(9), 2200-2203. https://doi.org/10.1021/ol200424x

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AB - Chemical equations presented. An efficient and unprecedented organocatalytic reaction of γ-nitroketones with α,β-unsaturated aldehydes to give polyfunctionalized [4.4.0] bicyclic skeletons was developed. The diphenylprolinol silyl ether mediated nitro-Michael/Aldol reaction afforded the hexa-substituted decalin carboaldehydes with excellent diastereo- and enantioselectivity (up to >99:1 dr and >99% ee) via a formal [4 + 2] carbocyclization process.

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10.1021/ol200424x