Chiral 1,2,5-triphenylphospholanium tetrafluoroborate as ligand precursor in Rh-catalyzed asymmetric hydrogenation of methyl (Z)-2-acetamidocinnamate

被引：12

作者：

Dobrota, C ^{[1
]}

Toffano, M ^{[1
]}

Fiaud, JC ^{[1
]}

机构：

[1] Univ Paris 11, Inst Chim Mol & Mat Orsay, CNRS, UMR 8075,Lab Catalyse Mol, F-91405 Orsay, France

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 44期

关键词：

asymmetric catalysis; P ligand; ligand design; hydrogenation; enantioselectivity;

D O I：

10.1016/j.tetlet.2004.09.031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(S,S)-1,2,5-Triphenylphospholanium tetrafluoroborate salt 2 was conveniently used as chiral ligand precursor in rhodium-catalyzed asymmetric hydrogenation of methyl (Z)-2-acetamidocinnamate. P-31 NMR showed the existence of a solvent-dependent equilibrium between the salt and the free phosphine. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：8153 / 8156

页数：4

共 8 条

[1]

BURK MJ, 2001, TETRAHEDRON-ASYMMETR, V2, P582

[2] P-Chirogenic phosphonium salts: preparation and use in Rh-catalyzed asymmetric hydrogenation of enamides [J].

Danjo, H ;

Sasaki, W ;

Miyazaki, T ;

Imamoto, T .

TETRAHEDRON LETTERS, 2003, 44 (17) :3467-3469

[3] PREPARATION OF OPTICALLY PURE 1,2,5-TRIPHENYLPHOSPHOLANE - USE AS LIGAND FOR ENANTIOSELECTIVE TRANSITION-METAL CATALYSIS [J].

FIAUD, JC ;

LEGROS, JY .

TETRAHEDRON LETTERS, 1991, 32 (38) :5089-5092

[4] Enantiomerically pure 1,2,5-triphenylphospholane through the synthesis and resolution of the chiral trans-(2,5)-diphenylphospholanic acid [J].

Guillen, F ;

Fiaud, JC .

TETRAHEDRON LETTERS, 1999, 40 (15) :2939-2942

[5] Synthesis and first applications of a new family of chiral monophosphine ligand: 2,5-diphenylphosphospholanes [J].

Guillen, F ;

Rivard, M ;

Toffano, M ;

Legros, JY ;

Daran, JC ;

Fiaud, JC .

TETRAHEDRON, 2002, 58 (29) :5895-5904

[6] Diastereoselective palladium-catalyzed formate reduction of allylic carbonates as a new entry into propionate units [J].

Lautens, M ;

Paquin, JF .

ORGANIC LETTERS, 2003, 5 (19) :3391-3394

[7] Synthesis of novel tetracycles via an intramolecular Heck reaction with anti-hydride elimination [J].

Lautens, M ;

Fang, YQ .

ORGANIC LETTERS, 2003, 5 (20) :3679-3682

[8] Air-stable trialkylphosphonium salts: Simple, practical, and versatile replacements for air-sensitive trialkylphosphines. Applications in stoichiometric and catalytic processes [J].

Netherton, MR ;

Fu, GC .

ORGANIC LETTERS, 2001, 3 (26) :4295-4298

← 1 →