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

Authors
  • Anwar, Shaik
  • Li, Shao Ming
  • Chen, Kwunmin
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Jun 06, 2014
Volume
16
Issue
11
Pages
2993–2995
Identifiers
DOI: 10.1021/ol501160k
PMID: 24835284
Source
Medline
License
Unknown

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.

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