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

doi:10.1021/ol202866h

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

Multidisciplinary chemistry

Research output: Contribution to journal › Article › peer-review

76 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 language	English
Pages (from-to)	6312-6315
Number of pages	4
Journal	Organic letters
Volume	13
Issue number	23
DOIs	https://doi.org/10.1021/ol202866h
Publication status	Published - Dec 2 2011

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol202866h

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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.",

author = "Hirohisa Ohmiya and Umi Yokobori and Yusuke Makida and Masaya Sawamura",

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T1 - General approach to allenes through copper-catalyzed γ-selective and stereospecific coupling between propargylic phosphates and alkylboranes

AU - Ohmiya, Hirohisa

AU - Yokobori, Umi

AU - Makida, Yusuke

AU - Sawamura, Masaya

PY - 2011/12/2

Y1 - 2011/12/2

N2 - 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.

AB - 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.

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

Abstract

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