Two-Pot Synthesis of Chiral 1,3-syn-Diols through Asymmetric Organocatalytic Aldol and Wittig Reactions Followed by Domino Hemiacetal/Oxy-Michael Reactions

Yujiro Hayashi, Takanobu Saitoh, Hiromu Arase, Genki Kawauchi, Naohiro Takeda, Yasuharu Shimasaki, Itaru Sato

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

A two-pot synthetic method to construct the chiral syn-1,3-diol unit has been developed from three aldehydes and either Wittig or Horner–Wadsworth–Emmons reagents. In the first pot, chiral δ-hydroxy α,β-unsaturated ketones are synthesized with excellent enantioselectivity by the organocatalyst-mediated asymmetric direct aldol reaction of two different aldehydes, followed by either Wittig or Horner–Wadsworth–Emmons reactions. In the second pot, domino acetalization with an aldehyde and subsequent oxy-Michael reaction proceeds in the presence of NaClO4 and a catalytic amount of Bi(OTf)3 (OTf=trifluoromethanesulfonate) to provide the chiral 1,3-syn-diol derivative with excellent diastereoselectivity. Diospongin C and yashabushidiol A have been synthesized efficiently by using the present method as a key step.

Original languageEnglish
Pages (from-to)4909-4915
Number of pages7
JournalChemistry - A European Journal
Volume24
Issue number19
DOIs
Publication statusPublished - 2018 Apr 3

Keywords

  • asymmetric synthesis
  • diols
  • domino reactions
  • organocatalysis
  • synthesis design

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Two-Pot Synthesis of Chiral 1,3-syn-Diols through Asymmetric Organocatalytic Aldol and Wittig Reactions Followed by Domino Hemiacetal/Oxy-Michael Reactions'. Together they form a unique fingerprint.

Cite this