Highly Enantioselective Iridium-Catalyzed Hydrogenation of Cyclic Enamides

被引：69

作者：

Salomo, Ernest ^{[1
]}

Orgue, Silvia ^{[1
]}

Riera, Antoni ^{[1
,2
]}

Verdaguer, Xavier ^{[1
,2
]}

机构：

[1] Barcelona Inst Sci & Technol, Inst Res Biomed IRB Barcelona, Baldiri Reixac 10, Barcelona 08028, Spain

[2] Univ Barcelona, Dept Quim Organ, Marti & Franques 1, E-08028 Barcelona, Spain

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 28期

关键词：

asymmetric hydrogenation; enamides; iridium; ligand design; P ligands; ASYMMETRIC HYDROGENATION; S(N)2-AT-P REACTIONS; LIGANDS; MECHANISM; ALKENES; OLEFINS; OXAZAPHOSPHOLIDINES; AMINOPHOSPHINES; TAUTOMERISM; COMPLEXES;

D O I：

10.1002/anie.201602219

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The MaxPHOX-Ir catalyst system provided the highest selectivity ever reported for the reduction of cyclic enamides derived from alpha-and beta-tetralones. This result indicates that iridium catalysts are also proficient in reducing alkenes bearing metal-coordinating groups. In the present system, selectivity was pressure-dependent: In most cases, a decrease in the H-2 pressure to 3 bar resulted in an increase in enantioselectivity. Moreover, the process can be carried out in environmentally friendly solvents, such as methanol and ethyl acetate, with no loss of selectivity.

引用

页码：7988 / 7992

页数：5

共 42 条

[41] Filling Gaps in Asymmetric Hydrogenation Methods for Acyclic Stereocontrol: Application to Chirons for Polyketide-Derived Natural Products [J].