Diastereoselective synthesis of quaternary alpha-amino acids from diketopiperazine templates

Stephen G. Davies; A. Christopher Garner; Jaqueline V. A. Ouzman; Paul M. Roberts; Andrew D. Smith; Emma J. Snow; James E. Thomson; Juan A. Tamayo; Richard J. Vickers

doi:10.1039/b704475e

Diastereoselective synthesis of quaternary alpha-amino acids from diketopiperazine templates

Stephen G. Davies, A. Christopher Garner, Jaqueline V. A. Ouzman, Paul M. Roberts, Andrew D. Smith, Emma J. Snow, James E. Thomson, Juan A. Tamayo, Richard J. Vickers

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

Abstract

Sequential enolate alkylations of (S)- N(1)-methyl-5-methoxy-6-isopropyl-3,6-dihydropyrazin-2-one and ( S)- N( 1)- p-methoxybenzyl-5-methoxy-6-isopropyl-3,6-dihydropyrazin-2-one proceed with excellent levels of diastereoselectivity (> 90% de) affording quaternary alpha-amino acids in high enantiomeric excess (> 98% ee) after deprotection and hydrolysis.

Original language	English
Pages (from-to)	2138-2147
Number of pages	10
Journal	Organic & Biomolecular Chemistry
Volume	5
Issue number	13
DOIs	https://doi.org/10.1039/b704475e
Publication status	Published - 2007

Keywords

X-RAY-ANALYSIS
EFFICIENT ENANTIOSELECTIVE SYNTHESIS
CHIRAL NONRACEMIC ENOLATE
PHASE-TRANSFER CATALYSIS
ASYMMETRIC-SYNTHESIS
STEREOSELECTIVE-SYNTHESIS
2,6-DIAMINOPIMELIC ACID
STEREOCONTROLLED SYNTHESIS
L-VALINE
IONIC LIQUIDS

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10.1039/b704475e

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@article{5a0a00b6fd2847ef92f97eed606b3138,

title = "Diastereoselective synthesis of quaternary alpha-amino acids from diketopiperazine templates",

abstract = "Sequential enolate alkylations of (S)- N(1)-methyl-5-methoxy-6-isopropyl-3,6-dihydropyrazin-2-one and ( S)- N( 1)- p-methoxybenzyl-5-methoxy-6-isopropyl-3,6-dihydropyrazin-2-one proceed with excellent levels of diastereoselectivity (> 90\% de) affording quaternary alpha-amino acids in high enantiomeric excess (> 98\% ee) after deprotection and hydrolysis.",

keywords = "X-RAY-ANALYSIS, EFFICIENT ENANTIOSELECTIVE SYNTHESIS, CHIRAL NONRACEMIC ENOLATE, PHASE-TRANSFER CATALYSIS, ASYMMETRIC-SYNTHESIS, STEREOSELECTIVE-SYNTHESIS, 2,6-DIAMINOPIMELIC ACID, STEREOCONTROLLED SYNTHESIS, L-VALINE, IONIC LIQUIDS",

author = "Davies, \{Stephen G.\} and Garner, \{A. Christopher\} and Ouzman, \{Jaqueline V. A.\} and Roberts, \{Paul M.\} and Smith, \{Andrew D.\} and Snow, \{Emma J.\} and Thomson, \{James E.\} and Tamayo, \{Juan A.\} and Vickers, \{Richard J.\}",

year = "2007",

doi = "10.1039/b704475e",

language = "English",

volume = "5",

pages = "2138--2147",

journal = "Organic \& Biomolecular Chemistry",

issn = "1477-0539",

publisher = "Royal Society of Chemistry",

number = "13",

}

TY - JOUR

T1 - Diastereoselective synthesis of quaternary alpha-amino acids from diketopiperazine templates

AU - Davies, Stephen G.

AU - Garner, A. Christopher

AU - Ouzman, Jaqueline V. A.

AU - Roberts, Paul M.

AU - Smith, Andrew D.

AU - Snow, Emma J.

AU - Thomson, James E.

AU - Tamayo, Juan A.

AU - Vickers, Richard J.

PY - 2007

Y1 - 2007

N2 - Sequential enolate alkylations of (S)- N(1)-methyl-5-methoxy-6-isopropyl-3,6-dihydropyrazin-2-one and ( S)- N( 1)- p-methoxybenzyl-5-methoxy-6-isopropyl-3,6-dihydropyrazin-2-one proceed with excellent levels of diastereoselectivity (> 90% de) affording quaternary alpha-amino acids in high enantiomeric excess (> 98% ee) after deprotection and hydrolysis.

AB - Sequential enolate alkylations of (S)- N(1)-methyl-5-methoxy-6-isopropyl-3,6-dihydropyrazin-2-one and ( S)- N( 1)- p-methoxybenzyl-5-methoxy-6-isopropyl-3,6-dihydropyrazin-2-one proceed with excellent levels of diastereoselectivity (> 90% de) affording quaternary alpha-amino acids in high enantiomeric excess (> 98% ee) after deprotection and hydrolysis.

KW - X-RAY-ANALYSIS

KW - EFFICIENT ENANTIOSELECTIVE SYNTHESIS

KW - CHIRAL NONRACEMIC ENOLATE

KW - PHASE-TRANSFER CATALYSIS

KW - ASYMMETRIC-SYNTHESIS

KW - STEREOSELECTIVE-SYNTHESIS

KW - 2,6-DIAMINOPIMELIC ACID

KW - STEREOCONTROLLED SYNTHESIS

KW - L-VALINE

KW - IONIC LIQUIDS

UR - https://www.scopus.com/pages/publications/34250703723

U2 - 10.1039/b704475e

DO - 10.1039/b704475e

M3 - Article

SN - 1477-0539

VL - 5

SP - 2138

EP - 2147

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 13

ER -

Diastereoselective synthesis of quaternary alpha-amino acids from diketopiperazine templates

Abstract

Keywords

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