The stereochemistry of transmetallation between allylstannanes and CH3SnCl3

Raymond L. Marshall, David J. Young

Research output: Contribution to journalArticleResearchpeer-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 languageEnglish
Pages (from-to)2369-2370
Number of pages2
JournalTetrahedron Letters
Volume33
Issue number17
DOIs
Publication statusPublished - 17 Apr 1992
Externally publishedYes

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Stereochemistry
Hydrolysis
Alcohols
Temperature
Water
benzaldehyde

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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.",
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The stereochemistry of transmetallation between allylstannanes and CH3SnCl3. / Marshall, Raymond L.; Young, David J.

In: Tetrahedron Letters, Vol. 33, No. 17, 17.04.1992, p. 2369-2370.

Research output: Contribution to journalArticleResearchpeer-review

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T1 - The stereochemistry of transmetallation between allylstannanes and CH3SnCl3

AU - Marshall, Raymond L.

AU - Young, David J.

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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.

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