Enantioselective Rh-catalyzed hydrogenation of enol acetates and enol carbamates with monodentate phosphoramidites

被引：70

作者：

Panella, L

Feringa, BL

de Vries, JG

Minnaard, AJ

机构：

[1] Univ Groningen, Dept Organ & Mol Inorgan Chem, Stratingh Inst, NL-9747 AG Groningen, Netherlands

[2] DSM Res & Patents, Life Sci Adv Synth, Catalysis & Dev, NL-6160 MD Geleen, Netherlands

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 19期

关键词：

D O I：

10.1021/ol051559c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Monodentate phosphoramidites, in particular PipPhos and its octahydro analogue, are excellent ligands for the rhodium-catalyzed asymmetric hydrogenation of aromatic enol acetates, enol carbamates, and 2-dienol carbamates up to 98% ee. These latter substrates were hydrogenated selectively to the carbamates of the allyl alcohol.

引用

收藏

页码：4177 / 4180

页数：4

相关论文

共 45 条

[11] Achiral ligands dramatically enhance rate and enantioselectivity in the Rh/phosphoramidite-catalyzed hydrogenation of α,β-disubstituted unsaturated acids [J].

Hoen, R ;

Boogers, JAF ;

Bernsmann, H ;

Minnaard, AJ ;

Meetsma, A ;

Tiemersma-Wegman, TD ;

de Vries, AHM ;

de Vries, JG ;

Feringa, BL .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (27) :4209-4212

[12] Catechol-based phosphoramidites: A new class of chiral ligands for rhodium-catalyzed asymmetric hydrogenations [J].

Hoen, R ;

van den Berg, M ;

Bernsmann, H ;

Minnaard, AJ ;

de Vries, JG ;

Feringa, BL .

ORGANIC LETTERS, 2004, 6 (09) :1433-1436

[13] CHEMISTRY OF CARBANIONS .23. USE OF METAL-COMPLEXES TO CONTROL ALDOL CONDENSATION [J].

HOUSE, HO ;

CRUMRINE, DS ;

TERANISH.AY ;

OLMSTEAD, HD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (10) :3310-3324

[14] Synthesis of new chiral monodentate phosphite ligands and their use in catalytic asymmetric hydrogenation [J].

Hua, ZH ;

Vassar, VC ;

Ojima, I .

ORGANIC LETTERS, 2003, 5 (21) :3831-3834

[15] Chiral monodentate phosphorus ligands for rhodium-catalyzed asymmetric hydrogenation [J].

Jerphagnon, T ;

Renaud, JL ;

Bruneau, C .

TETRAHEDRON-ASYMMETRY, 2004, 15 (14) :2101-2111

[16]

Jiang QZ, 1999, ANGEW CHEM INT EDIT, V38, P516, DOI 10.1002/(SICI)1521-3773(19990215)38:4<516::AID-ANIE516>3.0.CO

[17]

2-B

[18] The application of monodentate secondary phosphine oxide ligands in rhodium- and iridium-catalyzed asymmetric hydrogenation [J].

Jiang, XB ;

van den Berg, M ;

Minnaard, AJ ;

Feringa, BL ;

de Vries, JG .

TETRAHEDRON-ASYMMETRY, 2004, 15 (14) :2223-2229

[19]

JUNG ME, 1977, TETRAHEDRON LETT, P3791

[20]

Knowles WS, 2002, ANGEW CHEM INT EDIT, V41, P1999

← 1 2 3 4 5 →