Asymmetric Synthesis of a-Mercapto-b-Amino Acid Derivatives: Application to the Synthesis of Polysubstituted Thiomorpholines

J L Candela-Lena; S G Davies; P M Roberts; B Roux; A J Russell; E M Sanchez-Fernandez; Andrew David Smith; . .

doi:10.1016/j.tetasy.2006.04.004

Asymmetric Synthesis of a-Mercapto-b-Amino Acid Derivatives: Application to the Synthesis of Polysubstituted Thiomorpholines

J L Candela-Lena, S G Davies, P M Roberts, B Roux, A J Russell, E M Sanchez-Fernandez, Andrew David Smith, . .

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

Abstract

Tandem conjugate addition of homochiral lithium N-benzyl-N-(alpha-methyl-p-methoxybenzyl)amide to tert-butyl cinnamate and enolate trapping with (TsSBu)-Bu-t proceeds with high diastercoselectivity to give a homochiral anti-alpha-tert-butylthio-beta-amino ester. Stepwise deprotection gives the corresponding free alpha-tert-butylthio-beta-amino acid without epimerisation. Tandem conjugate addition of homochiral lithium N-allyl-N-(alpha-methylbenzyl)amide to tert-butyl cinnamate and enolate trapping with TsS'Bu followed by conversion of the S-tert-butyl group to a disulphide, and reduction with Lalancette's reagent generates polysubstituted thiomorpholine derivatives. (c) 2006 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	1135
Number of pages	1135
Journal	Tetrahedron: Asymmetry
Volume	17
DOIs	https://doi.org/10.1016/j.tetasy.2006.04.004
Publication status	Published - 3 Apr 2006

Keywords

NEUROTOXIN TYPE-B
POTENT INHIBITORS
ALLYLIC AMINES
AMMONIA EQUIVALENTS
CONJUGATE ADDITION
ORGANIC-SYNTHESIS
PROTECTING GROUP
PROTONATION
CLEAVAGE
EXCHANGE

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title = "Asymmetric Synthesis of a-Mercapto-b-Amino Acid Derivatives: Application to the Synthesis of Polysubstituted Thiomorpholines",

abstract = "Tandem conjugate addition of homochiral lithium N-benzyl-N-(alpha-methyl-p-methoxybenzyl)amide to tert-butyl cinnamate and enolate trapping with (TsSBu)-Bu-t proceeds with high diastercoselectivity to give a homochiral anti-alpha-tert-butylthio-beta-amino ester. Stepwise deprotection gives the corresponding free alpha-tert-butylthio-beta-amino acid without epimerisation. Tandem conjugate addition of homochiral lithium N-allyl-N-(alpha-methylbenzyl)amide to tert-butyl cinnamate and enolate trapping with TsS'Bu followed by conversion of the S-tert-butyl group to a disulphide, and reduction with Lalancette's reagent generates polysubstituted thiomorpholine derivatives. (c) 2006 Elsevier Ltd. All rights reserved.",

keywords = "NEUROTOXIN TYPE-B, POTENT INHIBITORS, ALLYLIC AMINES, AMMONIA EQUIVALENTS, CONJUGATE ADDITION, ORGANIC-SYNTHESIS, PROTECTING GROUP, PROTONATION, CLEAVAGE, EXCHANGE",

author = "Candela-Lena, {J L} and Davies, {S G} and Roberts, {P M} and B Roux and Russell, {A J} and Sanchez-Fernandez, {E M} and Smith, {Andrew David} and . .",

year = "2006",

month = apr,

day = "3",

doi = "10.1016/j.tetasy.2006.04.004",

language = "English",

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pages = "1135",

journal = "Tetrahedron: Asymmetry",

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T1 - Asymmetric Synthesis of a-Mercapto-b-Amino Acid Derivatives: Application to the Synthesis of Polysubstituted Thiomorpholines

AU - Candela-Lena, J L

AU - Davies, S G

AU - Roberts, P M

AU - Roux, B

AU - Russell, A J

AU - Sanchez-Fernandez, E M

AU - Smith, Andrew David

AU - ., .

PY - 2006/4/3

Y1 - 2006/4/3

N2 - Tandem conjugate addition of homochiral lithium N-benzyl-N-(alpha-methyl-p-methoxybenzyl)amide to tert-butyl cinnamate and enolate trapping with (TsSBu)-Bu-t proceeds with high diastercoselectivity to give a homochiral anti-alpha-tert-butylthio-beta-amino ester. Stepwise deprotection gives the corresponding free alpha-tert-butylthio-beta-amino acid without epimerisation. Tandem conjugate addition of homochiral lithium N-allyl-N-(alpha-methylbenzyl)amide to tert-butyl cinnamate and enolate trapping with TsS'Bu followed by conversion of the S-tert-butyl group to a disulphide, and reduction with Lalancette's reagent generates polysubstituted thiomorpholine derivatives. (c) 2006 Elsevier Ltd. All rights reserved.

AB - Tandem conjugate addition of homochiral lithium N-benzyl-N-(alpha-methyl-p-methoxybenzyl)amide to tert-butyl cinnamate and enolate trapping with (TsSBu)-Bu-t proceeds with high diastercoselectivity to give a homochiral anti-alpha-tert-butylthio-beta-amino ester. Stepwise deprotection gives the corresponding free alpha-tert-butylthio-beta-amino acid without epimerisation. Tandem conjugate addition of homochiral lithium N-allyl-N-(alpha-methylbenzyl)amide to tert-butyl cinnamate and enolate trapping with TsS'Bu followed by conversion of the S-tert-butyl group to a disulphide, and reduction with Lalancette's reagent generates polysubstituted thiomorpholine derivatives. (c) 2006 Elsevier Ltd. All rights reserved.

KW - NEUROTOXIN TYPE-B

KW - POTENT INHIBITORS

KW - ALLYLIC AMINES

KW - AMMONIA EQUIVALENTS

KW - CONJUGATE ADDITION

KW - ORGANIC-SYNTHESIS

KW - PROTECTING GROUP

KW - PROTONATION

KW - CLEAVAGE

KW - EXCHANGE

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U2 - 10.1016/j.tetasy.2006.04.004

DO - 10.1016/j.tetasy.2006.04.004

M3 - Article

VL - 17

SP - 1135

JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

ER -

Asymmetric Synthesis of a-Mercapto-b-Amino Acid Derivatives: Application to the Synthesis of Polysubstituted Thiomorpholines

Abstract

Keywords

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