A Novel One-Pot Stereoselective Synthesis of N-Protected α-Amino Acids from Morita-Baylis-Hillman Acetates

被引：13

作者：

Yadav, Lal Dhar Singh ^{[1
]}

Rai, Vijai Kumar ^{[1
]}

Singh, Santosh ^{[1
]}

机构：

[1] Univ Allahabad, Dept Chem, Green Synth Lab, Allahabad 211002, Uttar Pradesh, India

来源：

SYNLETT | 2009年 / 09期

关键词：

Morita-Baylis-Hillman reaction; S(N)2 reaction; alpha-amino acids; regio- and diastereoselective; one-pot synthesis; NUCLEOPHILIC-SUBSTITUTION; ALLYLIC AMINATION; FACILE SYNTHESIS; ADDUCTS; DERIVATIVES; CONSTRUCTION; BUTENOLIDES; CYCLIZATION; CONVERSION; CHEMISTRY;

D O I：

10.1055/s-0029-1217164

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first example of an operationally simple direct regio- and diastereoselective introduction of N-protected alpha-amino acids into Morita-Baylis-Hillman (MBH) acetates is reported. The DABCO-catalyzed reaction of MBH acetates with 2-phenyl-1,3-oxazol-5-one affords N-protected alpha-amino acids regioselectively in excellent yield (81-93%) with high diastereoselectivity (>92%) at ambient temperature. The synthetic protocol involves S(N)2'-S(N)2' reaction and water-driven ring-opening cascades in a one-pot procedure, which are salient features of the present investigation.

引用

页码：1423 / 1428

页数：6

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