Tris(trimethylsilyl) silane: an unprecedented enhancement in the diastereoselectivity of radical cyclisations to give 2,4-disubstituted piperidines

Lucile Gandon; Alexander Russell; John Snaith

doi:10.1039/b409714a

Tris(trimethylsilyl) silane: an unprecedented enhancement in the diastereoselectivity of radical cyclisations to give 2,4-disubstituted piperidines

Lucile Gandon
, Alexander Russell
, John Snaith

Chemistry

Research output: Contribution to journal › Article

16 Citations (Scopus)

Abstract

Cyclisation of bromides 4a-f mediated by tributyltin hydride affords predominantly the trans piperidines 5a-f with modest diastereomeric ratios, while cyclisation with tris(trimethylsilyl)silane affords the same products with diastereomeric ratios of up to 99:1.

Original language	English
Pages (from-to)	2270-2271
Number of pages	2
Journal	Organic and Biomolecular Chemistry
Volume	2
Issue number	16
DOIs	https://doi.org/10.1039/b409714a
Publication status	Published - 1 Jan 2004

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title = "Tris(trimethylsilyl) silane: an unprecedented enhancement in the diastereoselectivity of radical cyclisations to give 2,4-disubstituted piperidines",

abstract = "Cyclisation of bromides 4a-f mediated by tributyltin hydride affords predominantly the trans piperidines 5a-f with modest diastereomeric ratios, while cyclisation with tris(trimethylsilyl)silane affords the same products with diastereomeric ratios of up to 99:1.",

author = "Lucile Gandon and Alexander Russell and John Snaith",

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AU - Russell, Alexander

AU - Snaith, John

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N2 - Cyclisation of bromides 4a-f mediated by tributyltin hydride affords predominantly the trans piperidines 5a-f with modest diastereomeric ratios, while cyclisation with tris(trimethylsilyl)silane affords the same products with diastereomeric ratios of up to 99:1.

AB - Cyclisation of bromides 4a-f mediated by tributyltin hydride affords predominantly the trans piperidines 5a-f with modest diastereomeric ratios, while cyclisation with tris(trimethylsilyl)silane affords the same products with diastereomeric ratios of up to 99:1.

UR - https://www.scopus.com/pages/publications/4644278317

U2 - 10.1039/b409714a

DO - 10.1039/b409714a

M3 - Article

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EP - 2271

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 16

ER -

Tris(trimethylsilyl) silane: an unprecedented enhancement in the diastereoselectivity of radical cyclisations to give 2,4-disubstituted piperidines

Abstract

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