Chelating Hydroxyalkyl NHC as Efficient Chiral Ligands for Room-Temperature Copper-Catalyzed Asymmetric Allylic Alkylation

被引：20

作者：

Jennequin, Thomas ^{[1
,2
]}

Wencel-Delord, Joanna ^{[1
,2
]}

Rix, Diane ^{[1
,2
]}

Daubignard, Julien ^{[1
,2
]}

Crevisy, Christophe ^{[1
,2
]}

Mauduit, Marc ^{[1
,2
]}

机构：

[1] Ecole Natl Super Chim Rennes, CNRS, UMR 6226, F-35708 Rennes 7, France

[2] Univ Europeenne Bretagne, F-35000 Rennes, France

来源：

SYNLETT | 2010年 / 11期

关键词：

chiral chelating diaminocarbene; asymmetric allylic alkylation; copper dialkylzinc; N-HETEROCYCLIC CARBENES; ENANTIOSELECTIVE SYNTHESIS; CONJUGATE ADDITION; STEREOGENIC CENTERS; METATHESIS; ALKYLZINC; REAGENTS; DESIGN;

D O I：

10.1055/s-0029-1220127

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The application of chiral chelating hydroxy NHC in copper-catalyzed asymmetric allylic alkylation (Cu-AAA) involving various dialkylzincs and allylic phosphate substrates is reported here. From a library of 11 chiral chelating hydroxyalkyl NHC, a fine-tuning has been done to identify the best architectural features enabling to produce the expected g-adducts in total regioselectivity, good isolated yields, and excellent enantioselectivities (ranging from 93% to >98% ee).

引用

页码：1661 / 1665

页数：5