Asymmetric one-pot four-component coupling reaction: Synthesis of substituted tetrahydropyrans catalyzed by diphenylprolinol silyl ether

Hayato Ishikawa, Satoshi Sawano, Yusuke Yasui, Yusuke Shibata, Yujiro Hayashi

Research output: Contribution to journalArticlepeer-review

63 Citations (Scopus)

Abstract

(Chemical Equation Presented) Domino effect: The title reaction uses an asymmetric Michael/Henry reaction/acetalization/Lewis acid mediated allylation reaction to provide highly substituted tetrahydropyrans with excellent enantioselectivity (see scheme; TMS=trimethylsilyl). All the carbon atoms in the tetrahydropyran ring are substituted with different groups, and the relative and absolute stereochemistry of the five contiguous carbon centers are completely controlled.

Original languageEnglish
Pages (from-to)3774-3779
Number of pages6
JournalAngewandte Chemie - International Edition
Volume50
Issue number16
DOIs
Publication statusPublished - 2011 Apr 11
Externally publishedYes

Keywords

  • Asymmetric synthesis
  • Domino reactions
  • Michael addition
  • Multicomponent reactions
  • Organocatalysis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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