Trading N and O. Part 4: Asymmetric synthesis of syn-β-substituted-α-amino acids

被引：6

作者：

Davies, Stephen G. ^{[1
]}

Fletcher, Ai M. ^{[1
]}

Greenaway, Catherine J. ^{[1
]}

Kennedy, Matthew S. ^{[1
]}

Mayer, Christoph ^{[1
]}

Roberts, Paul M. ^{[1
]}

Thomson, James E. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Mansfield Rd, Oxford OX1 3TA, England

来源：

TETRAHEDRON | 2018年 / 74卷 / 38期

关键词：

beta-Substituted-alpha-amino acid; beta-Hydroxy-alpha-amino acid; beta-Fluoro-alpha-amino acid; Aziridinium ion; Lithium amide; Asymmetric synthesis; DYNAMIC KINETIC RESOLUTION; STEREOSELECTIVE-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; ALDOL REACTIONS; HYDROXY; ESTERS; DERIVATIVES; 1,2,3,4-TETRAHYDROISOQUINOLINES; ERYTHRO-3-FLUOROPHENYLALANINE; THREO-3-FLUOROPHENYLALANINE;

D O I：

10.1016/j.tet.2018.04.071

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A total of nine enantiopure syn-beta-substituted-alpha-amino acids have been synthesised, comprising both syn-beta-hydroxy-alpha-amino acids and syn-beta-fluoro-alpha-amino acids. The key step in the synthetic strategy towards these syn-beta-substituted-alpha-amino acids involves a stereospecific rearrangement, which proceeds via the intermediacy of the corresponding aziridinium ions. The requisite enantiopure syn-alpha-hydroxy-beta-amino esters were prepared via asymmetric aminohydroxylation of the corresponding alpha,beta-unsaturated esters followed by epimerisation of the resultant anti-alpha-hydroxy-beta-amino esters at the C(2)-position. Subsequent activation of the alpha-hydroxy moiety as a leaving group followed by displacement by the beta-amino substituent gave the corresponding aziridinium species. Regioselective in situ ring-opening of the aziridinium intermediates with either water or fluoride gave the corresponding syn-beta-hydroxy-alpha-amino ester or syn-beta-fluoro-alpha-amino ester, respectively, and N-deprotection and ester hydrolysis afforded the target syn-beta-substituted-alpha-amino acids as single diastereoisomers in good overall yield. (C) 2018 Published by Elsevier Ltd.

引用

页码：5049 / 5061

页数：13

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