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

44 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

Fingerprint Dive into the research topics of 'Directed intermolecular carbomagnesation across vinylsilanes: 2-PyMe<sub>2</sub>Si group as a removable directing group'. Together they form a unique fingerprint.

Cite this

@article{9b17dd7f82e54b8cab63181b60bab7f8,

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.",

keywords = "Alcohols, Magnesium, Multicomponent reactions, Silicon, Synthetic methods",

author = "Kenichiro Itami and Koichi Mitsudo and Yoshida, {Jun Ichi}",

year = "2001",

month = jun,

day = "18",

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

language = "English",

volume = "40",

pages = "2337--2339",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "12",

}

TY - JOUR

T1 - Directed intermolecular carbomagnesation across vinylsilanes

T2 - 2-PyMe2Si group as a removable directing group

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

UR - http://www.scopus.com/inward/record.url?scp=0035907933&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035907933&partnerID=8YFLogxK

U2 - 10.1002/1521-3773(20010618)40:12<2337::AID-ANIE2337>3.0.CO;2-Q

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

M3 - Article

AN - SCOPUS:0035907933

VL - 40

SP - 2337

EP - 2339

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 12

ER -