Aldehyde addition to allylic stannanes via a transmetallation pathway

Stereocontrol in the absence of internal coordination

Raymond L. Marshall, I. Wayan Muderawan, David J. Young

Research output: Contribution to journalArticleResearchpeer-review

Abstract

Methyltin trichloride and indium(III) chloride promote the addition of aldehydes to cyclic allylic stannanes providing good yields of the corresponding homoallylic alcohols. These reactions proceed via an initial transmetallation involving anti approach of the electrophile, followed by syn aldehyde addition that is erythro selective. These Lewis acids do not promote the corresponding addition of imines, rather providing the same homoallylic alcohols after an in situ aqueous hydrolysis. Imine addition is possible with boron trifluoride-diethyl ether as the Lewis acid.

Original languageEnglish
Pages (from-to)957-962
Number of pages6
JournalJournal of the Chemical Society. Perkin Transactions 2
Volume2000
Issue number5
DOIs
Publication statusPublished - 1 May 2000
Externally publishedYes

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Lewis Acids
Imines
Aldehydes
Alcohols
Ether
Chlorides
Hydrolysis
stannane
methyltin
indium trichloride
boron trifluoride

Cite this

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abstract = "Methyltin trichloride and indium(III) chloride promote the addition of aldehydes to cyclic allylic stannanes providing good yields of the corresponding homoallylic alcohols. These reactions proceed via an initial transmetallation involving anti approach of the electrophile, followed by syn aldehyde addition that is erythro selective. These Lewis acids do not promote the corresponding addition of imines, rather providing the same homoallylic alcohols after an in situ aqueous hydrolysis. Imine addition is possible with boron trifluoride-diethyl ether as the Lewis acid.",
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Aldehyde addition to allylic stannanes via a transmetallation pathway : Stereocontrol in the absence of internal coordination. / Marshall, Raymond L.; Muderawan, I. Wayan; Young, David J.

In: Journal of the Chemical Society. Perkin Transactions 2, Vol. 2000, No. 5, 01.05.2000, p. 957-962.

Research output: Contribution to journalArticleResearchpeer-review

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T1 - Aldehyde addition to allylic stannanes via a transmetallation pathway

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AU - Marshall, Raymond L.

AU - Muderawan, I. Wayan

AU - Young, David J.

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U2 - 10.1039/B000435I

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