Stereodivergent Hydroboration of Allenes

Yoshiyuki Nagashima, Keiji Sasaki, Takahiro Suto, Takaaki Sato, Noritaka Chida

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

Full details of a stereodivergent hydroboration of allenes are reported. While hydroboration of an allene with 9-BBN provided a thermodynamically stable (E)-allylic alcohol after oxidative work-up, the reaction of an identical allene with HB(Sia)2 (disiamylborane) formed a (Z)-allylic alcohol as the kinetic product. The developed conditions allowed for the synthesis of trisubstituted olefins in a highly stereoselective fashion, which is known to be challenging. The method was also applied to the stereodivergent synthesis of structural motifs such as skipped dienes and allylbenzenes, which are often embedded in biologically active natural products.

Original languageEnglish
Pages (from-to)1024-1028
Number of pages5
JournalChemistry - An Asian Journal
Volume13
Issue number8
DOIs
Publication statusPublished - 2018 Apr 16

Keywords

  • allenes
  • hydroboration
  • natural products
  • skipped dienes
  • stereoselectivity

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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