Chiral phosphites and phosphoramidites based on the tropane skeleton and their application in catalysis

被引：39

作者：

Cramer, N ^{[1
]}

Laschat, S ^{[1
]}

Baro, A ^{[1
]}

机构：

[1] Univ Stuttgart, Inst Organ Chem, D-60569 Stuttgart, Germany

来源：

ORGANOMETALLICS | 2006年 / 25卷 / 09期

关键词：

D O I：

10.1021/om0510066

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A class of novel BINOL-containing tropanes was accessible by treating enantiopure (6S)-configured tropinone acetals 5a and 8 with chlorophosphites 7. When applied to Cu-catalyzed 1,4-additions of dialkylzinc to cyclic and acyclic enones 14 and 16, the bidentate phosphoramidite (S,S)-9a bearing two (S)-binaphthol units worked selectively in most cases (up to 90% ee). (S,S)-9a was also superior to the other ligands in Rh-mediated hydrogenations of dimethyl itaconate 18 and methyl acetamidocinnamate 20 (85% ee and 95% ee). In both reactions, a matched/mismatched case was observed for (S,S)-9a and its congener (R,R)-9a.

引用

页码：2284 / 2291

页数：8

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