Stereoselective U-4CRs with 1-amino-5-desoxy-5-thio-2,3,4-O-isobutanoyl-β-D-xylopyranose -: an effective and selectively removable chiral auxiliary

被引：73

作者：

Ross, GF ^{[1
]}

Herdtweck, E ^{[1
]}

Ugi, I ^{[1
]}

机构：

[1] Tech Univ Munich, D-85747 Garching, Germany

来源：

TETRAHEDRON | 2002年 / 58卷 / 30期

关键词：

stereoselective Ugi four component reaction; chiral auxiliary; chiral amine component; amino thiocarbohydrate; alpha-amino acid derivatives;

D O I：

10.1016/S0040-4020(02)00484-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Ugi four component reaction (U-4CR) offers a short and direct route for the synthesis of alpha-amino acid and peptide derivatives. With 1-amino-5-desoxy-5-thio-2,3,4-O-isobutanoyl-beta-D-xylopyranose as a chiral amine component excellent chemical yields and stereoselectivities are obtained. After the U-4CR the chiral auxiliary can be cleaved off selectively under mild conditions. The configuration of one of the products was confirmed by X-ray analysis. (C) 2002 Published by Elsevier Science Ltd.

引用

页码：6127 / 6133

页数：7

共 49 条

[11]

EMERSON DW, 1971, TETRAHEDRON LETT, P3445

[12] ON ENANTIOMORPH-POLARITY ESTIMATION [J].