The stereochemistry of transmetallation between allylstannanes and CH3SnCl3

Raymond L. Marshall; David J. Young

doi:10.1016/S0040-4039(00)74214-6

The stereochemistry of transmetallation between allylstannanes and CH₃SnCl₃

Raymond L. Marshall, David J. Young

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

Abstract

The addition of CH₃SnCl₃ to isomeric mixtures of allylstannane (1) proceeds stereospecifically with anti approach of the electrophile in CD₂Cl₂ at -78°C but is less selective in CDCl₃ at room temperature. The corresponding reaction of crotyltrimethylstannane (CD₂Cl₂, -78°C) indicates initial γ attack. Addition of CH₃SnCl₃ to allyltributylstannane (CDCl₃,r.t.) followed by benzaldehyde and water hydrolysis yields the expected honoallyl alcohol quantitatively.

Original language	English
Pages (from-to)	2369-2370
Number of pages	2
Journal	Tetrahedron Letters
Volume	33
Issue number	17
DOIs	https://doi.org/10.1016/S0040-4039(00)74214-6
Publication status	Published - 17 Apr 1992
Externally published	Yes

Access to Document

10.1016/S0040-4039(00)74214-6

Link to publication in Scopus

Fingerprint Dive into the research topics of 'The stereochemistry of transmetallation between allylstannanes and CH<sub>3</sub>SnCl<sub>3</sub>'. Together they form a unique fingerprint.

Cite this

@article{6d2cdeee65fd45098dd2710d24d9a85c,

title = "The stereochemistry of transmetallation between allylstannanes and CH3SnCl3",

abstract = "The addition of CH3SnCl3 to isomeric mixtures of allylstannane (1) proceeds stereospecifically with anti approach of the electrophile in CD2Cl2 at -78°C but is less selective in CDCl3 at room temperature. The corresponding reaction of crotyltrimethylstannane (CD2Cl2, -78°C) indicates initial γ attack. Addition of CH3SnCl3 to allyltributylstannane (CDCl3,r.t.) followed by benzaldehyde and water hydrolysis yields the expected honoallyl alcohol quantitatively.",

author = "Marshall, {Raymond L.} and Young, {David J.}",

year = "1992",

month = apr,

day = "17",

doi = "10.1016/S0040-4039(00)74214-6",

language = "English",

volume = "33",

pages = "2369--2370",

journal = "Tetrahedron Letters: the international journal for the rapid publication of all preliminary communications in organic chemistry",

issn = "0040-4039",

publisher = "Elsevier",

number = "17",

}

TY - JOUR

T1 - The stereochemistry of transmetallation between allylstannanes and CH3SnCl3

AU - Marshall, Raymond L.

AU - Young, David J.

PY - 1992/4/17

Y1 - 1992/4/17

N2 - The addition of CH3SnCl3 to isomeric mixtures of allylstannane (1) proceeds stereospecifically with anti approach of the electrophile in CD2Cl2 at -78°C but is less selective in CDCl3 at room temperature. The corresponding reaction of crotyltrimethylstannane (CD2Cl2, -78°C) indicates initial γ attack. Addition of CH3SnCl3 to allyltributylstannane (CDCl3,r.t.) followed by benzaldehyde and water hydrolysis yields the expected honoallyl alcohol quantitatively.

AB - The addition of CH3SnCl3 to isomeric mixtures of allylstannane (1) proceeds stereospecifically with anti approach of the electrophile in CD2Cl2 at -78°C but is less selective in CDCl3 at room temperature. The corresponding reaction of crotyltrimethylstannane (CD2Cl2, -78°C) indicates initial γ attack. Addition of CH3SnCl3 to allyltributylstannane (CDCl3,r.t.) followed by benzaldehyde and water hydrolysis yields the expected honoallyl alcohol quantitatively.

UR - http://www.scopus.com/inward/record.url?scp=0026573431&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)74214-6

DO - 10.1016/S0040-4039(00)74214-6

M3 - Article

AN - SCOPUS:0026573431

VL - 33

SP - 2369

EP - 2370

JO - Tetrahedron Letters: the international journal for the rapid publication of all preliminary communications in organic chemistry

JF - Tetrahedron Letters: the international journal for the rapid publication of all preliminary communications in organic chemistry

SN - 0040-4039

IS - 17

ER -