Highly cis-Selective Rh(I)-Catalyzed Cyclopropanation Reactions

被引：37

作者：

Rosenberg, Marianne Lenes ^{[2
]}

Vlasana, Klara ^{[2
]}

Sen Gupta, Nalinava ^{[2
]}

Wragg, David ^{[2
]}

Tilset, Mats ^{[1
]}

机构：

[1] CTCC, Dept Chem, N-0315 Oslo, Norway

[2] Univ Oslo, Dept Chem, N-0315 Oslo, Norway

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 08期

关键词：

ASYMMETRIC CYCLOPROPANATION; DIRHODIUM(II) COMPLEXES; ETHYL DIAZOACETATE; OLEFINS; CATALYST; DIASTEREOCONTROL; ENANTIOCONTROL; CONSTRUCTION; OPTIMIZATION; DERIVATIVES;

D O I：

10.1021/jo102140z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The performance of recently reported highly cis-diastereoselective Rh(I) cyclopropanation catalysts has been significantly improved by a systematic study of different reaction parameters (catalyst activation, solvent, temperature, stoichiometry). The catalyst efficiency and diastereoselectivity were enhanced by changing the activating agent from AgOTf to NaBArf. With this new system, the Rh(I) catalyst was shown to be a highly efficient and cis-diastereoselective cyclopropanation catalyst in reactions between alpha-diazoacetates and a range of different alkenes and substituted derivatives. Particularly noteworthy is the remarkable reactivity and cis-diastereoselectivity displayed in the reactions between ethyl diazoacetate and cyclopentene, 2,5-dihydrofuran, and benzofuran, with yields up to 99% and cis-selectivities greater than 99%.

引用

页码：2465 / 2470

页数：6

共 45 条

[11] REACTIONS OF (CO)5WCHC6H5 WITH ALKENES [J].