Homochiral Lithium Amides for the Asymmetric Synthesis of b-Amino Acids

S G Davies; N M Garrido; D Kruchinin; O Ichihara; L J Kotchie; P D Price; A J Price-Mortimer; A J Russell; Andrew David Smith

doi:10.1016/j.tetasy.2006.05.008

Homochiral Lithium Amides for the Asymmetric Synthesis of b-Amino Acids

S G Davies, N M Garrido, D Kruchinin, O Ichihara, L J Kotchie, P D Price, A J Price-Mortimer, A J Russell, Andrew David Smith

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

Abstract

Secondary homochiral lithium amides derived from a-methylbenzylamine undergo highly diastereoselective conjugate additions to a range of alpha,beta-unsaturated esters. The corresponding beta-amino acids are readily liberated by successive N-debenzylation and ester hydrolysis, furnishing (R)-beta-amino butyric acid, (R)-beta-amino pentanoic acid, (S)-beta-leucine, (R)-beta-amino octanoic acid, (S)-beta-phenylalanine, (S)-beta-tyrosine methyl ether, (S)-beta-tyrosine hydrochloride and (S)-beta-(2-methoxyphenyl)-beta-amino propanoic acid in high yields and high ee. The application of this procedure to the synthesis of the natural products (R)-beta-DOPA and (R)-beta-lysine is demonstrated. The development of a simplified one-pot reaction protocol applicable to the multi-gram scale synthesis of homochiral beta-amino esters is also delineated. (c) 2006 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	1793
Number of pages	1793
Journal	Tetrahedron: Asymmetry
Volume	17
DOIs	https://doi.org/10.1016/j.tetasy.2006.05.008
Publication status	Published - 31 Jul 2006

Keywords

ENANTIOSELECTIVE SYNTHESIS
CONJUGATE ADDITION
ORGANIC-SYNTHESIS
ALPHA,BETA-UNSATURATED ESTERS
MICHAEL ADDITIONS
STEREOSELECTIVE-SYNTHESIS
NITROGEN NUCLEOPHILES
PRACTICAL SYNTHESIS
IRON COMPLEXES
MARINE SPONGE

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.tetasy.2006.05.008

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title = "Homochiral Lithium Amides for the Asymmetric Synthesis of b-Amino Acids",

abstract = "Secondary homochiral lithium amides derived from a-methylbenzylamine undergo highly diastereoselective conjugate additions to a range of alpha,beta-unsaturated esters. The corresponding beta-amino acids are readily liberated by successive N-debenzylation and ester hydrolysis, furnishing (R)-beta-amino butyric acid, (R)-beta-amino pentanoic acid, (S)-beta-leucine, (R)-beta-amino octanoic acid, (S)-beta-phenylalanine, (S)-beta-tyrosine methyl ether, (S)-beta-tyrosine hydrochloride and (S)-beta-(2-methoxyphenyl)-beta-amino propanoic acid in high yields and high ee. The application of this procedure to the synthesis of the natural products (R)-beta-DOPA and (R)-beta-lysine is demonstrated. The development of a simplified one-pot reaction protocol applicable to the multi-gram scale synthesis of homochiral beta-amino esters is also delineated. (c) 2006 Elsevier Ltd. All rights reserved.",

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author = "Davies, {S G} and Garrido, {N M} and D Kruchinin and O Ichihara and Kotchie, {L J} and Price, {P D} and Price-Mortimer, {A J} and Russell, {A J} and Smith, {Andrew David}",

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month = jul,

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doi = "10.1016/j.tetasy.2006.05.008",

language = "English",

volume = "17",

pages = "1793",

journal = "Tetrahedron: Asymmetry",

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T1 - Homochiral Lithium Amides for the Asymmetric Synthesis of b-Amino Acids

AU - Davies, S G

AU - Garrido, N M

AU - Kruchinin, D

AU - Ichihara, O

AU - Kotchie, L J

AU - Price, P D

AU - Price-Mortimer, A J

AU - Russell, A J

AU - Smith, Andrew David

PY - 2006/7/31

Y1 - 2006/7/31

N2 - Secondary homochiral lithium amides derived from a-methylbenzylamine undergo highly diastereoselective conjugate additions to a range of alpha,beta-unsaturated esters. The corresponding beta-amino acids are readily liberated by successive N-debenzylation and ester hydrolysis, furnishing (R)-beta-amino butyric acid, (R)-beta-amino pentanoic acid, (S)-beta-leucine, (R)-beta-amino octanoic acid, (S)-beta-phenylalanine, (S)-beta-tyrosine methyl ether, (S)-beta-tyrosine hydrochloride and (S)-beta-(2-methoxyphenyl)-beta-amino propanoic acid in high yields and high ee. The application of this procedure to the synthesis of the natural products (R)-beta-DOPA and (R)-beta-lysine is demonstrated. The development of a simplified one-pot reaction protocol applicable to the multi-gram scale synthesis of homochiral beta-amino esters is also delineated. (c) 2006 Elsevier Ltd. All rights reserved.

AB - Secondary homochiral lithium amides derived from a-methylbenzylamine undergo highly diastereoselective conjugate additions to a range of alpha,beta-unsaturated esters. The corresponding beta-amino acids are readily liberated by successive N-debenzylation and ester hydrolysis, furnishing (R)-beta-amino butyric acid, (R)-beta-amino pentanoic acid, (S)-beta-leucine, (R)-beta-amino octanoic acid, (S)-beta-phenylalanine, (S)-beta-tyrosine methyl ether, (S)-beta-tyrosine hydrochloride and (S)-beta-(2-methoxyphenyl)-beta-amino propanoic acid in high yields and high ee. The application of this procedure to the synthesis of the natural products (R)-beta-DOPA and (R)-beta-lysine is demonstrated. The development of a simplified one-pot reaction protocol applicable to the multi-gram scale synthesis of homochiral beta-amino esters is also delineated. (c) 2006 Elsevier Ltd. All rights reserved.

KW - ENANTIOSELECTIVE SYNTHESIS

KW - CONJUGATE ADDITION

KW - ORGANIC-SYNTHESIS

KW - ALPHA,BETA-UNSATURATED ESTERS

KW - MICHAEL ADDITIONS

KW - STEREOSELECTIVE-SYNTHESIS

KW - NITROGEN NUCLEOPHILES

KW - PRACTICAL SYNTHESIS

KW - IRON COMPLEXES

KW - MARINE SPONGE

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U2 - 10.1016/j.tetasy.2006.05.008

DO - 10.1016/j.tetasy.2006.05.008

M3 - Article

VL - 17

SP - 1793

JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

ER -

Homochiral Lithium Amides for the Asymmetric Synthesis of b-Amino Acids

Abstract

Keywords

UN SDGs

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