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

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

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Marshall, R. L., & Young, D. J. (1992). The stereochemistry of transmetallation between allylstannanes and CH₃SnCl₃. Tetrahedron Letters, 33(17), 2369-2370. https://doi.org/10.1016/S0040-4039(00)74214-6

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