PINACOL COUPLING OF ALIPHATIC-ALDEHYDES PROMOTED BY NIOBIUM-(III) REAGENT

被引：33

作者：

SZYMONIAK, J

BESANCON, J

MOISE, C

机构：

[1] Laboratoire de Synthèse, d'Electrosynthèse Organométalliques associé au CNRS (URA 1685), Faculté des Sciences, 21000 Dijon

来源：

TETRAHEDRON | 1994年 / 50卷 / 09期

关键词：

NB(III) REAGENT; PINACOL COUPLING; ACETALIZATION; STEREOSELECTIVITY;

D O I：

10.1016/S0040-4020(01)86997-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

NbCl3 (DME) was found to be a useful reagent for the intermolecular pinacol coupling of aliphatic aldehydes. The high anti diastereoselectivity of this reaction (dl/meso greater than or equal to 9/l) did nor depend on the variation in the aldehyde alkyl chain. With respect to intramolecular pinacolization, the loss of the stereoselectivity observed is consistent with the mechanism involving an insertion of the era-group into the metal-carbon bond of the intermediate niobiooxirane.

引用

页码：2841 / 2848

页数：8

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