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

Teresa M. Cokley; Neil S. Isaacs; Adam McCluskey; David J. Young

doi:10.1515/MGMC.1997.20.9.581

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

Teresa M. Cokley, Neil S. Isaacs, Adam McCluskey, David J. Young

Research output: Contribution to journal › Article

Abstract

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.

Original language	English
Pages (from-to)	581-582
Number of pages	2
Journal	Main Group Metal Chemistry
Volume	20
Issue number	9
DOIs	https://doi.org/10.1515/MGMC.1997.20.9.581
Publication status	Published - 1 Sep 1997
Externally published	Yes

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abstract = "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.",

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AU - Young, David J.

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AB - 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.

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