Asymmetric synthesis of α-amino carbonyls (aldehydes, ketones and acids) using lithium (R)-N-benzyl-N-α-methylbenzylamide

S. G. Davies; S. W. Epstein; O. Ichihara; A. D. Smith

doi:10.1055/s-2001-17449

Asymmetric synthesis of α-amino carbonyls (aldehydes, ketones and acids) using lithium (R)-N-benzyl-N-α-methylbenzylamide

S. G. Davies^*, S. W. Epstein, O. Ichihara, A. D. Smith

^*Corresponding author for this work

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

Abstract

The diastereoselective conjugate addition of lithium (R)-N-benzyl-N-α-methylbenzylamide to α,β-unsaturated esters and subsequent enolate hydroxylation, followed by reduction and oxidative cleavage provides a facile route to N,N-protected α-amino aldehydes and ketones. Further manipulation furnishes α-amino acids in high enantiomeric excess.

Original language	English
Pages (from-to)	1599-1601
Number of pages	3
Journal	Synlett
Issue number	10
DOIs	https://doi.org/10.1055/s-2001-17449
Publication status	Published - 1 Jan 2001

Keywords

Asymmetric synthesis
Conjugate addition
Lithium amides
α-amino acid
α-amino aldehyde
β-amino acids

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10.1055/s-2001-17449

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title = "Asymmetric synthesis of α-amino carbonyls (aldehydes, ketones and acids) using lithium (R)-N-benzyl-N-α-methylbenzylamide",

abstract = "The diastereoselective conjugate addition of lithium (R)-N-benzyl-N-α-methylbenzylamide to α,β-unsaturated esters and subsequent enolate hydroxylation, followed by reduction and oxidative cleavage provides a facile route to N,N-protected α-amino aldehydes and ketones. Further manipulation furnishes α-amino acids in high enantiomeric excess.",

keywords = "Asymmetric synthesis, Conjugate addition, Lithium amides, α-amino acid, α-amino aldehyde, β-amino acids",

author = "Davies, \{S. G.\} and Epstein, \{S. W.\} and O. Ichihara and Smith, \{A. D.\}",

year = "2001",

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doi = "10.1055/s-2001-17449",

language = "English",

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TY - JOUR

T1 - Asymmetric synthesis of α-amino carbonyls (aldehydes, ketones and acids) using lithium (R)-N-benzyl-N-α-methylbenzylamide

AU - Davies, S. G.

AU - Epstein, S. W.

AU - Ichihara, O.

AU - Smith, A. D.

PY - 2001/1/1

Y1 - 2001/1/1

N2 - The diastereoselective conjugate addition of lithium (R)-N-benzyl-N-α-methylbenzylamide to α,β-unsaturated esters and subsequent enolate hydroxylation, followed by reduction and oxidative cleavage provides a facile route to N,N-protected α-amino aldehydes and ketones. Further manipulation furnishes α-amino acids in high enantiomeric excess.

AB - The diastereoselective conjugate addition of lithium (R)-N-benzyl-N-α-methylbenzylamide to α,β-unsaturated esters and subsequent enolate hydroxylation, followed by reduction and oxidative cleavage provides a facile route to N,N-protected α-amino aldehydes and ketones. Further manipulation furnishes α-amino acids in high enantiomeric excess.

KW - Asymmetric synthesis

KW - Conjugate addition

KW - Lithium amides

KW - α-amino acid

KW - α-amino aldehyde

KW - β-amino acids

UR - https://www.scopus.com/pages/publications/0034805349

U2 - 10.1055/s-2001-17449

DO - 10.1055/s-2001-17449

M3 - Article

AN - SCOPUS:0034805349

SN - 0936-5214

SP - 1599

EP - 1601

JO - Synlett

JF - Synlett

IS - 10

ER -

Asymmetric synthesis of α-amino carbonyls (aldehydes, ketones and acids) using lithium (R)-N-benzyl-N-α-methylbenzylamide

Abstract

Keywords

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