Organocatalytic synthesis of substituted spirocyclohexane carbaldehydes via [4 + 2] annulation strategy between 2-arylideneindane-1,3-diones and glutaraldehyde

Shaik Anwar, Shao Ming Li, Kwunmin Chen

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

An organocatalytic domino reaction between 2-arylideneindane-1,3-diones and glutaraldehyde has been devised that gives functionalized spirocyclohexane carbaldehydes with an all-carbon quaternary center. The reaction proceeds through a Michael/Aldol sequence in good-to-high chemical yields and with high levels of stereoselectivity (up to >95:5 dr and 99% ee) in the presence of the α,α-l-diphenylprolinol trimethylsilyl ether 3 (20 mol %) and DIPEA (20 mol %) in ether at 0 °C.

Original languageEnglish
Pages (from-to)2993-2995
Number of pages3
JournalOrganic Letters
Volume16
Issue number11
DOIs
Publication statusPublished - 2014 Jun 6

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Stereoselectivity
Glutaral
Dione
Ether
ethers
Carbon
synthesis
carbon
diphenylprolinol trimethylsilyl ether
N,N-diisopropylethylamine
3-hydroxybutanal

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Organocatalytic synthesis of substituted spirocyclohexane carbaldehydes via [4 + 2] annulation strategy between 2-arylideneindane-1,3-diones and glutaraldehyde. / Anwar, Shaik; Li, Shao Ming; Chen, Kwunmin.

In: Organic Letters, Vol. 16, No. 11, 06.06.2014, p. 2993-2995.

Research output: Contribution to journalArticle

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