Remote asymmetric induction reactions and wide range stereocontrol strategy for synthesis of polypropionates

Research output: Contribution to journalReview articlepeer-review

6 Citations (Scopus)

Abstract

In 2004 we reported an anti-selective remote asymmetric induction reaction using chiral vinyl- ketene silyl Ar,Oacetal 1 (the stereoselective vinylogous Mukaiyama aldol reaction). The reaction has been applied to natural product synthesis by many groups since the reaction makes syntheses short and efficient by simultaneous introduction of both asymmetric centers and the multiply functionalized carbon chain. Recently, we have developed a variety of remote asymmetric induction reactions using the £.£-vinylketene Ar,0-Acetal 1. Additionally, we have developed a new strategy to synthesize polypropionates in short steps by combining remote asymmetric induction reactions and functionalization of double bonds. In this paper, the new strategy as well as new remote asymmetric induction reactions and their applications to syntheses of polypropionates are described.

Original languageEnglish
Pages (from-to)831-849
Number of pages19
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume75
Issue number8
DOIs
Publication statusPublished - 2017

Keywords

  • Acylation
  • Alkylation
  • Bromination
  • Polyketide library
  • Polypropionate
  • Remote asymmetric induction
  • Total synthesis
  • Vinylogous mukaiyama aldol reaction

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Remote asymmetric induction reactions and wide range stereocontrol strategy for synthesis of polypropionates'. Together they form a unique fingerprint.

Cite this