General approach to allenes through copper-catalyzed γ-selective and stereospecific coupling between propargylic phosphates and alkylboranes

Hirohisa Ohmiya, Umi Yokobori, Yusuke Makida, Masaya Sawamura

Research output: Contribution to journalArticle

62 Citations (Scopus)

Abstract

Copper-catalyzed γ-selective coupling between propargylic phosphates and alkylboron compounds (alkyl-9-BBN, prepared by hydroboration of alkenes with 9-BBN-H) affords multisubstituted allenes with various functional groups. The reaction of enantioenriched propargylic phosphates to give axially chiral allenes proceeds with excellent point-to-axial chirality transfer with 1,3-anti stereochemistry.

Original languageEnglish
Pages (from-to)6312-6315
Number of pages4
JournalOrganic Letters
Volume13
Issue number23
DOIs
Publication statusPublished - Dec 2 2011

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Copper
phosphates
alkyl compounds
Phosphates
hydroboration
copper
Stereochemistry
Chirality
stereochemistry
Alkenes
chirality
Functional groups
alkenes
propadiene
9-borabicyclo(3,3,1)nonane

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

General approach to allenes through copper-catalyzed γ-selective and stereospecific coupling between propargylic phosphates and alkylboranes. / Ohmiya, Hirohisa; Yokobori, Umi; Makida, Yusuke; Sawamura, Masaya.

In: Organic Letters, Vol. 13, No. 23, 02.12.2011, p. 6312-6315.

Research output: Contribution to journalArticle

Ohmiya, Hirohisa ; Yokobori, Umi ; Makida, Yusuke ; Sawamura, Masaya. / General approach to allenes through copper-catalyzed γ-selective and stereospecific coupling between propargylic phosphates and alkylboranes. In: Organic Letters. 2011 ; Vol. 13, No. 23. pp. 6312-6315.
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