AN ASYMMETRIC-SYNTHESIS OF A 3-HYDROXY-BETA-LACTAM BY KETENE-IMINE CYCLOADDITION - UTILIZATION OF CHIRAL KETENES FROM CARBOHYDRATES

被引：34

作者：

BORER, BC ^{[1
]}

BALOGH, DW ^{[1
]}

机构：

[1] ELI LILLY & CO,LILLY RES LAB,INDIANAPOLIS,IN 46285

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 08期

关键词：

D O I：

10.1016/S0040-4039(00)74481-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Staudinger reaction of a chiral carbohydrate-based ketene and an imine proceeds to give, after removal of the sugar, cis-3-hydroxy-beta-lactam 7 in moderate yield with good asymmetric induction (70% e.e.).

引用

页码：1039 / 1040

页数：2

共 5 条

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[2] UNSATURATED CARBOHYDRATES .9. SYNTHESIS OF 2,3-DIDEOXY-ALPHA-D-ERYTHRO-HEX-2-ENOPYRANOSIDES FROM TRI-O-ACETYL-D-GLUCAL
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[3] A TOTAL SYNTHESIS OF NOCARDICINS
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[J]. TETRAHEDRON, 1983, 39 (15) : 2591 - 2597
[4] SYNTHESIS OF BETA-LACTAMS FROM SUGAR VINYL ETHERS AND ISOCYANATES
KALUZA, Z
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[J]. TETRAHEDRON LETTERS, 1989, 30 (38) : 5171 - 5172
[5] PIRKLE W, 1986, J AM CHEM SOC, P352

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