Asymmetric synthesis of 3,4,5,6-tetrasubstituted piperidin-2-ones by three-component coupling

Stephen G. Davies; Andrew D. Smith; Andrew R. Cowley

doi:10.1055/s-2004-830887

Asymmetric synthesis of 3,4,5,6-tetrasubstituted piperidin-2-ones by three-component coupling

Stephen G. Davies^*, Andrew D. Smith, Andrew R. Cowley

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

The asymmetric three-component coupling of α,β-unsaturated esters and alkylidene malonates initiated with a homochiral lithium amide proceeds with high levels of diastereoselectivity, with hydrogenation of the resultant α-substituted β-amino acid derivatives giving a range of differentially protected 3,4,5,6-tetrasubstituted piperidinones with four contiguous stereogenic centres.

Original language	English
Pages (from-to)	1957-1960
Number of pages	4
Journal	Synlett
Issue number	11
DOIs	https://doi.org/10.1055/s-2004-830887
Publication status	Published - 6 Sept 2004

Keywords

Conjugate addition
Oligomerisation
Piperidin-2-one
Three component coupling

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10.1055/s-2004-830887

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title = "Asymmetric synthesis of 3,4,5,6-tetrasubstituted piperidin-2-ones by three-component coupling",

abstract = "The asymmetric three-component coupling of α,β-unsaturated esters and alkylidene malonates initiated with a homochiral lithium amide proceeds with high levels of diastereoselectivity, with hydrogenation of the resultant α-substituted β-amino acid derivatives giving a range of differentially protected 3,4,5,6-tetrasubstituted piperidinones with four contiguous stereogenic centres.",

keywords = "Conjugate addition, Oligomerisation, Piperidin-2-one, Three component coupling",

author = "Davies, {Stephen G.} and Smith, {Andrew D.} and Cowley, {Andrew R.}",

year = "2004",

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doi = "10.1055/s-2004-830887",

language = "English",

pages = "1957--1960",

journal = "Synlett",

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AU - Davies, Stephen G.

AU - Smith, Andrew D.

AU - Cowley, Andrew R.

PY - 2004/9/6

Y1 - 2004/9/6

N2 - The asymmetric three-component coupling of α,β-unsaturated esters and alkylidene malonates initiated with a homochiral lithium amide proceeds with high levels of diastereoselectivity, with hydrogenation of the resultant α-substituted β-amino acid derivatives giving a range of differentially protected 3,4,5,6-tetrasubstituted piperidinones with four contiguous stereogenic centres.

AB - The asymmetric three-component coupling of α,β-unsaturated esters and alkylidene malonates initiated with a homochiral lithium amide proceeds with high levels of diastereoselectivity, with hydrogenation of the resultant α-substituted β-amino acid derivatives giving a range of differentially protected 3,4,5,6-tetrasubstituted piperidinones with four contiguous stereogenic centres.

KW - Conjugate addition

KW - Oligomerisation

KW - Piperidin-2-one

KW - Three component coupling

UR - http://www.scopus.com/inward/record.url?scp=4544265900&partnerID=8YFLogxK

U2 - 10.1055/s-2004-830887

DO - 10.1055/s-2004-830887

M3 - Article

AN - SCOPUS:4544265900

SN - 0936-5214

SP - 1957

EP - 1960

JO - Synlett

JF - Synlett

IS - 11

ER -

Asymmetric synthesis of 3,4,5,6-tetrasubstituted piperidin-2-ones by three-component coupling

Abstract

Keywords

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