Directed intermolecular carbomagnesation across vinylsilanes: 2-PyMe2Si group as a removable directing group

Kenichiro Itami; Koichi Mitsudo; Jun Ichi Yoshida

doi:10.1002/1521-3773(20010618)40:12<2337::AID-ANIE2337>3.0.CO;2-Q

Directed intermolecular carbomagnesation across vinylsilanes: 2-PyMe₂Si group as a removable directing group

Kenichiro Itami, Koichi Mitsudo, Jun Ichi Yoshida

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

45 Citations (Scopus)

Abstract

Facile addition of primary alkyl Gridnard reagents to vinylsilanes has been realized for the first time by exploiting the directing effect of a 2-pridyl group on silicon [Eq. (1)]. Three-component coupling reactions of a Grignard reagent, the vinylsilane, and an electrophile, followed by oxidative removal of the 2-pyridyldimethylsilyl group with H₂O₂ furnishes various secondary alcohols in excellent overall yields.

Original language	English
Pages (from-to)	2337-2339
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	40
Issue number	12
DOIs	https://doi.org/10.1002/1521-3773(20010618)40:12<2337::AID-ANIE2337>3.0.CO;2-Q
Publication status	Published - Jun 18 2001
Externally published	Yes

Keywords

Alcohols
Magnesium
Multicomponent reactions
Silicon
Synthetic methods

ASJC Scopus subject areas

Catalysis
Chemistry(all)

Access to Document

10.1002/1521-3773(20010618)40:12<2337::AID-ANIE2337>3.0.CO;2-Q

Cite this

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title = "Directed intermolecular carbomagnesation across vinylsilanes: 2-PyMe2Si group as a removable directing group",

abstract = "Facile addition of primary alkyl Gridnard reagents to vinylsilanes has been realized for the first time by exploiting the directing effect of a 2-pridyl group on silicon [Eq. (1)]. Three-component coupling reactions of a Grignard reagent, the vinylsilane, and an electrophile, followed by oxidative removal of the 2-pyridyldimethylsilyl group with H2O2 furnishes various secondary alcohols in excellent overall yields.",

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AU - Itami, Kenichiro

AU - Mitsudo, Koichi

AU - Yoshida, Jun Ichi

PY - 2001/6/18

Y1 - 2001/6/18

N2 - Facile addition of primary alkyl Gridnard reagents to vinylsilanes has been realized for the first time by exploiting the directing effect of a 2-pridyl group on silicon [Eq. (1)]. Three-component coupling reactions of a Grignard reagent, the vinylsilane, and an electrophile, followed by oxidative removal of the 2-pyridyldimethylsilyl group with H2O2 furnishes various secondary alcohols in excellent overall yields.

AB - Facile addition of primary alkyl Gridnard reagents to vinylsilanes has been realized for the first time by exploiting the directing effect of a 2-pridyl group on silicon [Eq. (1)]. Three-component coupling reactions of a Grignard reagent, the vinylsilane, and an electrophile, followed by oxidative removal of the 2-pyridyldimethylsilyl group with H2O2 furnishes various secondary alcohols in excellent overall yields.

KW - Alcohols

KW - Magnesium

KW - Multicomponent reactions

KW - Silicon

KW - Synthetic methods

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