PINACOL CROSS-COUPLING OF 2-[N-(ALKOXYCARBONYL)AMINO] ALDEHYDES AND ALIPHATIC-ALDEHYDES BY [V2CL3(THF)(6)](2)[ZN2CL6] - SYNTHESIS OF SYN,SYN-3-[N-(ALKOXYCARBONYL)AMINO] 1,2-DIOLS

被引：100

作者：

KONRADI, AW ^{[1
]}

KEMP, SJ ^{[1
]}

PEDERSEN, SF ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1994年 / 116卷 / 04期

关键词：

D O I：

10.1021/ja00083a017

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Slow addition of 2-[N-(alkoxycarbonyl)amino] aldehydes to mixtures of [V2Cl3(THF)(6)](2)[Zn2Cl6] and aliphatic aldehydes gave syn,syn-3-[N-(alkoxycarbonyl)amino] 1,2-diols in good yield and high enantiomeric purity (>99:1). The alkyl group of the N-alkoxycarbonyl was shown to influence the yield: Me>allyl>Bn>t-Bu. Only the syn,syn diastereomer was observed (>20:1), except with N-Cbz-alaninal (10:1:1), O-benzyl-N-Cbz-serinal (7:1), and N-Cbz-prolinal (5:1 to 12:1). A new serinal derivative, N-Cbz-O-TBS-serinal, was cross coupled with n-pentadecanal to give a derivative of xylo-D-C-18-phytosphingosine.

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页码：1316 / 1323

页数：8

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