Synthesis of a new chiral amino phosphine ligand and its application in the asymmetric allylic alkylation (AAA) reaction

被引：28

作者：

Feng, Jianqing ^{[1
]}

Bohle, D. Scott ^{[1
]}

Li, Chao-Jun ^{[1
]}

机构：

[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada

来源：

TETRAHEDRON-ASYMMETRY | 2007年 / 18卷 / 09期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/j.tetasy.2007.05.005

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

This article describes the synthesis of a new chiral amino phosphine ligand based on an amino naphthol starting material, which is resolved efficiently by using L-tartaric acid. The asymmetric induction of the ligand in the Pd(0)-catalyzed allylic substitution of 1,3-diphenylprop-2-en-1-yl acetate with dimethyl malonate was investigated. Good yields and enantiomeric excesses up to 78% of the product were obtained. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：1043 / 1047

页数：5

共 37 条

[1] Steric hindrance versus asymmetric induction: new PN-ligands for carbon-carbon coupling reactions [J].

Bourghida, M ;

Widhalm, M .

TETRAHEDRON-ASYMMETRY, 1998, 9 (06) :1073-1083

[2]

BROWN J, 1995, TETRAHEDRON, V50, P4493

[3] Enantioselective palladium catalyzed allylic substitution with new chiral pyridine-phosphine ligands [J].

Brunel, JM ;

Constantieux, T ;

Labande, A ;

Lubatti, F ;

Buono, G .

TETRAHEDRON LETTERS, 1997, 38 (34) :5971-5974

[4] The application of Pd-complexes of trans-2,5-dialkylpyrrolidinyl-benzyldiphenylphosphines to enantioselective allylic alkylation [J].

Cahill, JP ;

Guiry, PJ .

TETRAHEDRON-ASYMMETRY, 1998, 9 (24) :4301-4305

[5] SYNTHESIS OF CHIRAL 2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL (BINAP) VIA A NOVEL NICKEL-CATALYZED PHOSPHINE INSERTION [J].

CAI, DW ;

PAYACK, JF ;

BENDER, DR ;

HUGHES, DL ;

VERHOEVEN, TR ;

REIDER, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (23) :7180-7181

[6] Chiral P,N-ligands with pyridine-nitrogen and phosphorus donor atoms.: Syntheses and applications in asymmetric catalysis [J].

Chelucci, G ;

Orrù, G ;

Pinna, GA .

TETRAHEDRON, 2003, 59 (48) :9471-9515

[7] ASYMMETRIC PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION USING PHOSPHORUS-CONTAINING OXAZOLINE LIGANDS [J].

DAWSON, GJ ;

FROST, CG ;

WILLIAMS, JMJ .

TETRAHEDRON LETTERS, 1993, 34 (19) :3149-3150

[8] Enantioselective allylic substitution using a novel (phosphino-1,3-oxazine)palladium catalyst [J].

Evans, PA ;

Brandt, TA .

TETRAHEDRON LETTERS, 1996, 37 (51) :9143-9146

[9] The development of bidentate P,N ligands for asymmetric catalysis [J].

Guiry, PJ ;

Saunders, CP .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (05) :497-537

[10] Enantioselective palladium-catalyzed allylic substitutions with asymmetric chiral ligands [J].

Helmchen, G .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :203-214

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