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Diphenylprolinol silyl ether as a catalyst in an asymmetric, catalytic, and direct michael reaction of nitroethanol with alpha,beta-unsaturated aldehydes

Academic Article
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Overview

authors

  • Gotoh, Hiroaki
  • Okamura, D.
  • Ishikawa, H.
  • Hayashi, Y.

publication date

  • September 2009

journal

  • Organic Letters  Journal

abstract

  • Diphenylprolinol silyl ether was found to be an effective organocatalyst in the enantioselective and direct Michael reaction of nitroethanol and alpha,beta-unsaturated aldehydes, affording the 1-hydroxy-trans-3,4-disubstituted tetrahydropyrans after isomerization. The generated Michael addition products are useful synthetic intermediates, which can be converted into chiral tetrahydropyran with a quaternary stereocenter, 3-substituted cis- and trans-prolines, and alpha-amino acid derivatives.

subject areas

  • Aldehydes
  • Animals
  • Catalysis
  • Ethers
  • Proline
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Identity

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol901483x

PubMed ID

  • 19739683
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Additional Document Info

start page

  • 4056

end page

  • 4059

volume

  • 11

issue

  • 18

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