High pressure allylstannane addition to α-amino aldehydes: Syn diastereoselectivity in the absence of chelation control

T M Cokley; N S Isaacs; A McCluskey; David James Young

doi:10.1515/MGMC.1997.20.9.581

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High pressure allylstannane addition to α-amino aldehydes: Syn diastereoselectivity in the absence of chelation control

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High pressure allylstannane addition to α-amino aldehydes: Syn diastereoselectivity in the absence of chelation control

T M Cokley, N S Isaacs, A McCluskey and David James Young

Main Group Metal Chemistry, Vol.20(9), pp.581-582

1997

DOI: https://doi.org/10.1515/MGMC.1997.20.9.581

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Abstract

diastereoselectivity

Contrary to expectations, the high pressure (9 kbar, 30°C) mediated addition of allyltrimethylstannane (2) to α-amino aldehydes (1) proceeds via an anti - Felkin - Anh mode to provide predominantly (60-88%) syn homoallylic alcohols. The diastereoselectivity of this reaction is dependent on the amino aldehyde side chain.

Details

Title: High pressure allylstannane addition to α-amino aldehydes: Syn diastereoselectivity in the absence of chelation control
Authors: T M Cokley (Author) - Griffith University
N S Isaacs (Author) - University of Reading, United Kingdom
A McCluskey (Author) - University of Newcastle
David James Young (Author) - Griffith University
Publication details: Main Group Metal Chemistry, Vol.20(9), pp.581-582
Publisher: Walter de Gruyter GmbH & Co. KG
Date published: 1997
DOI: 10.1515/MGMC.1997.20.9.581
ISSN: 0792-1241
Organisation Unit: University of the Sunshine Coast, Queensland
Language: English
Record Identifier: 99449173502621
Output Type: Journal article

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