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 | |
| Publication status | Published - Jun 18 2001 |
| Externally published | Yes |
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Keywords
- Alcohols
- Magnesium
- Multicomponent reactions
- Silicon
- Synthetic methods
ASJC Scopus subject areas
- Chemistry(all)
Cite this
Directed intermolecular carbomagnesation across vinylsilanes : 2-PyMe2Si group as a removable directing group. / Itami, Kenichiro; Mitsudo, Koichi; Yoshida, Jun Ichi.
In: Angewandte Chemie - International Edition, Vol. 40, No. 12, 18.06.2001, p. 2337-2339.Research output: Contribution to journal › Article
}
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
VL - 40
SP - 2337
EP - 2339
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 12
ER -