Construction of homoallylic alcohols from terminal alkynes and aldehydes with installation of syn-stereochemistry

Tomoya Miura; Yui Nishida; Masahiro Murakami

doi:10.1021/ja502169d

Construction of homoallylic alcohols from terminal alkynes and aldehydes with installation of syn-stereochemistry

Tomoya Miura, Yui Nishida, Masahiro Murakami

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

28 Citations (Scopus)

Abstract

A cationic rhodium(I) catalyst turns 2-silyl-1-alkenylboronate, readily prepared from a terminal alkyne, into the corresponding allylboronate species, which immediately undergoes nucleophilic addition to an aldehyde to give a syn-homoallylic alcohol stereoselectively.

Original language	English
Pages (from-to)	6223-6226
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	136
Issue number	17
DOIs	https://doi.org/10.1021/ja502169d
Publication status	Published - Apr 30 2014
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja502169d

Cite this

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title = "Construction of homoallylic alcohols from terminal alkynes and aldehydes with installation of syn-stereochemistry",

abstract = "A cationic rhodium(I) catalyst turns 2-silyl-1-alkenylboronate, readily prepared from a terminal alkyne, into the corresponding allylboronate species, which immediately undergoes nucleophilic addition to an aldehyde to give a syn-homoallylic alcohol stereoselectively.",

author = "Tomoya Miura and Yui Nishida and Masahiro Murakami",

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AU - Miura, Tomoya

AU - Nishida, Yui

AU - Murakami, Masahiro

PY - 2014/4/30

Y1 - 2014/4/30

N2 - A cationic rhodium(I) catalyst turns 2-silyl-1-alkenylboronate, readily prepared from a terminal alkyne, into the corresponding allylboronate species, which immediately undergoes nucleophilic addition to an aldehyde to give a syn-homoallylic alcohol stereoselectively.

AB - A cationic rhodium(I) catalyst turns 2-silyl-1-alkenylboronate, readily prepared from a terminal alkyne, into the corresponding allylboronate species, which immediately undergoes nucleophilic addition to an aldehyde to give a syn-homoallylic alcohol stereoselectively.

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M3 - Article

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Construction of homoallylic alcohols from terminal alkynes and aldehydes with installation of syn-stereochemistry

Abstract

ASJC Scopus subject areas

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