Palladium-catalyzed coupling reaction of propargylic oxiranes with arylboronic acids in aqueous media

Masahiro Yoshida; Hirofumi Ueda; Masataka Ihara

doi:10.1016/j.tetlet.2005.07.134

Palladium-catalyzed coupling reaction of propargylic oxiranes with arylboronic acids in aqueous media

Masahiro Yoshida, Hirofumi Ueda, Masataka Ihara

PHA - Molecular Pharmaceutical Science

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

57 Citations (Scopus)

Abstract

A novel type of coupling reaction has been developed by the palladium-catalyzed reaction of propargylic oxiranes with arylboronic acids, in which anti-substituted 4-aryl-2,3-allenols were produced in a highly diastereoselective manner. A chiral-substituted allene has been synthesized from the reaction of a chiral propargylic oxirane without loss of the chirality.

Original language	English
Pages (from-to)	6705-6708
Number of pages	4
Journal	Tetrahedron Letters
Volume	46
Issue number	39
DOIs	https://doi.org/10.1016/j.tetlet.2005.07.134
Publication status	Published - 2005 Sept 26

Keywords

Addition
Boronic acids
Oxiranes
Palladium
Propargylic compounds

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2005.07.134

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title = "Palladium-catalyzed coupling reaction of propargylic oxiranes with arylboronic acids in aqueous media",

abstract = "A novel type of coupling reaction has been developed by the palladium-catalyzed reaction of propargylic oxiranes with arylboronic acids, in which anti-substituted 4-aryl-2,3-allenols were produced in a highly diastereoselective manner. A chiral-substituted allene has been synthesized from the reaction of a chiral propargylic oxirane without loss of the chirality.",

keywords = "Addition, Boronic acids, Oxiranes, Palladium, Propargylic compounds",

author = "Masahiro Yoshida and Hirofumi Ueda and Masataka Ihara",

note = "Funding Information: This study was supported in part by a Grant-in-Aid for the Encouragement for Young Scientists (B) from the Japan Society for the Promotion of Science (JSPS) (for M.Y.). Copyright: Copyright 2008 Elsevier B.V., All rights reserved.",

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doi = "10.1016/j.tetlet.2005.07.134",

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T1 - Palladium-catalyzed coupling reaction of propargylic oxiranes with arylboronic acids in aqueous media

AU - Yoshida, Masahiro

AU - Ueda, Hirofumi

AU - Ihara, Masataka

N1 - Funding Information: This study was supported in part by a Grant-in-Aid for the Encouragement for Young Scientists (B) from the Japan Society for the Promotion of Science (JSPS) (for M.Y.). Copyright: Copyright 2008 Elsevier B.V., All rights reserved.

PY - 2005/9/26

Y1 - 2005/9/26

N2 - A novel type of coupling reaction has been developed by the palladium-catalyzed reaction of propargylic oxiranes with arylboronic acids, in which anti-substituted 4-aryl-2,3-allenols were produced in a highly diastereoselective manner. A chiral-substituted allene has been synthesized from the reaction of a chiral propargylic oxirane without loss of the chirality.

AB - A novel type of coupling reaction has been developed by the palladium-catalyzed reaction of propargylic oxiranes with arylboronic acids, in which anti-substituted 4-aryl-2,3-allenols were produced in a highly diastereoselective manner. A chiral-substituted allene has been synthesized from the reaction of a chiral propargylic oxirane without loss of the chirality.

KW - Addition

KW - Boronic acids

KW - Oxiranes

KW - Palladium

KW - Propargylic compounds

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DO - 10.1016/j.tetlet.2005.07.134

M3 - Article

AN - SCOPUS:23944505184

SN - 0040-4039

VL - 46

SP - 6705

EP - 6708

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 39

ER -

Palladium-catalyzed coupling reaction of propargylic oxiranes with arylboronic acids in aqueous media

Abstract

Keywords

ASJC Scopus subject areas

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