Direct Synthesis of β-Hydroxy-α-amino Acids via Diastereoselective Decarboxylative Aldol Reaction

被引：30

作者：

Singjunla, Yuttapong ^{[1
]}

Baudoux, Jerome ^{[1
]}

Rouden, Jacques ^{[1
]}

机构：

[1] ENSICAEN Univ Caen, Lab Chim Mol & Thioorgan, CNRS, Inst Normand Chim Mol Med & Macromol INC3M, F-14050 Caen, France

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 22期

关键词：

ASYMMETRIC TRANSFER HYDROGENATION; HALF-THIOESTERS; ENANTIOSELECTIVE SYNTHESIS; POLYKETIDE SYNTHASES; EFFICIENT; ESTERS; 1,4-ADDITION; GLYCINE; ANALOGS; COMPLEX;

D O I：

10.1021/ol402805f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A straightforward metal-free synthesis of anti-beta-hydroxy-alpha-amino acids is described. The organic base-mediated decarboxylative aldol reaction of cheap, readily available alpha-amidohemimalonates with various aldehydes afforded under very mild conditions anti-beta-hydroxy-alpha-amido esters in high yields and complete diastereoselectivity. Simple one-pot subsequent transformations enabled the corresponding anti-beta-hydroxy-alpha-amino acids or in a few examples their syn diastereomers to be obtained directly using epimerization conditions.

引用

页码：5770 / 5773

页数：4

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