PINACOL HOMOCOUPLING OF (S)-2-[N-(BENZYLOXYCARBONYL)AMINO] ALDEHYDES BY [V2CL3(THF)6]2[ZN2CL6] - SYNTHESIS OF C2-SYMMETRICAL (1S,2R,3R,4S)-1,4-DIAMINO 2,3-DIOLS

被引：77

作者：

KONRADI, AW ^{[1
]}

PEDERSEN, SF ^{[1
]}

机构：

[1] UNIV CALIF BERKELEY,DEPT CHEM,BERKELEY,CA 94720

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 01期

关键词：

D O I：

10.1021/jo00027a009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Six (S)-2-[N-(benzyloxycarbonyl)amino] aldehydes 3a-f were homocoupled by [V2Cl3(THF)6]2[Zn2Cl6] (1) to give C2-symmetric (1S,2R,3R,4S)-1,4-bis[N-(benzyloxycarbonyl)amino] 2,3-diols 4a-f in good yield. High-yield conversions of the diols to bisoxazolidinones (sodium hydride, tetrahydrofuran) and to the deprotected (1S,2R,3R,4S)-1,4-diamino 2,3-diol dihydrochloride salts (10% Pd/C, formic acid, HCl in ether) were performed.

引用

页码：28 / 32

页数：5

共 31 条

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