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
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
收藏
页码:6127 / 6133
页数:7
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