Synthesis of chiral cyclic nitrones via a nitrosoketene intermediate and their use for the complete EPC synthesis of nonproteinogenic amino acids

被引：45

作者：

Katagiri, N

Okada, M

Kaneko, C

机构：

[1] TOHOKU UNIV,INST PHARMACEUT,SENDAI,MIYAGI 98077,JAPAN

[2] YAMANOUCHI PHARMACEUT CO LTD,TSUKUBA RES LABS,TSUKUBA,IBARAKI 305,JAPAN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 11期

关键词：

D O I：

10.1016/0040-4039(96)00122-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New cyclic chiral nitrones constituting tw diastereomers were synthesized by the reaction of isonitroso Meldrum's acid with l-menthone via a nitrosoketene intermediate. Both nitrones reacted with allyltrimethylsilane diastereoselectively to give the corresponding isoxazolidine derivatives as sole products, which were converted to (S)- and (R)- allylglycines in ca. 100% ee, respectively.

引用

页码：1801 / 1804

页数：4

共 8 条

[1]

BLACK S, 1955, J BIOL CHEM, V213, P39

[2] ISOLATION AND BIOSYNTHESIS OF CYCLOPENTENYLGLYCINE, A NOVEL NON-PROTEINOGENIC AMINO-ACID IN FLACOURTIACEAE [J].