Organocatalytic synthesis of multiple substituted b[4.4.0]decalin system

Shaik Anwar, Hui Ju Chang, Kwunmin Chen

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)2200-2203
Number of pages4
JournalOrganic Letters
Volume13
Issue number9
DOIs
Publication statusPublished - 2011 May 6

Fingerprint

Michael reaction
Enantioselectivity
aldehydes
musculoskeletal system
Skeleton
Aldehydes
ethers
synthesis
3-hydroxybutanal
diphenylprolinol silyl ether
decalin

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Organocatalytic synthesis of multiple substituted b[4.4.0]decalin system. / Anwar, Shaik; Chang, Hui Ju; Chen, Kwunmin.

In: Organic Letters, Vol. 13, No. 9, 06.05.2011, p. 2200-2203.

Research output: Contribution to journalArticle

Anwar, Shaik ; Chang, Hui Ju ; Chen, Kwunmin. / Organocatalytic synthesis of multiple substituted b[4.4.0]decalin system. In: Organic Letters. 2011 ; Vol. 13, No. 9. pp. 2200-2203.
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