Highly efficient kinetic resolution of 2-cyclohexenyl acetate in Pd-catalyzed allylic alkylation

被引：82

作者：

Longmire, JM ^{[1
]}

Wang, B ^{[1
]}

Zhang, XM ^{[1
]}

机构：

[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 29期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(00)00844-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new phosphine ligand has been synthesized and employed in the Pd-catalyzed alkylation of 2-cyclohexenyl esters. A very efficient resolution of 2-cyclohexenyl acetate was observed during alkylation. In addition, the reactivity and enantioselectivity showed a strong dependence on the acetate salt with the BSA/MOAc (M = alkali metal) base system during alkyation of cyclohexenyl carbonate. (C) 2000 Published by Elsevier Science Ltd.

引用

页码：5435 / 5439

页数：5

共 37 条

[1] On the role of planar chirality in asymmetric catalysis:: A study toward appropriate ferrocene ligands for diethylzinc additions [J].

Bolm, C ;

Muñiz-Fernández, K ;

Seger, A ;

Raabe, G ;

Günther, K .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :7860-7867

[2] 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

[3] Robust and catalytically active mono- and bis-Pd-complexes of the 'Trost modular ligand' [J].

Butts, CP ;

Crosby, J ;

Lloyd-Jones, GC ;

Stephen, SC .

CHEMICAL COMMUNICATIONS, 1999, (17) :1707-1708

[4]

Dierkes P, 1998, ANGEW CHEM INT EDIT, V37, P3116, DOI 10.1002/(SICI)1521-3773(19981204)37:22<3116::AID-ANIE3116>3.0.CO

[5]

2-S

[6]

El Gihani MT, 1998, SYNTHESIS-STUTTGART, P357

[7] TO WHAT EXTENT IS A PI-ALLYLIC INTERMEDIATE INVOLVED IN SOME PALLADIUM-CATALYZED ALKYLATIONS [J].

FIAUD, JC ;

MALLERON, JL .

TETRAHEDRON LETTERS, 1981, 22 (15) :1399-1402

[8] Synthesis of an enantiomerically pure aminoisoquinocarbazole with antiarrhythmic activity via lipase-catalyzed enantioselective transesterification [J].

Fukazawa, T ;

Shimoji, Y ;

Hashimoto, T .

TETRAHEDRON-ASYMMETRY, 1996, 7 (06) :1649-1658

[9] Pd-catalyzed asymmetric synthesis of allylic tert-butyl sulfones and sulfides:: Kinetic resolution of the allylic substrate by a chiral Pd-complex [J].

Gais, HJ ;

Eichelmann, H ;

Spalthoff, N ;

Gerhards, F ;

Frank, M ;

Raabe, G .

TETRAHEDRON-ASYMMETRY, 1998, 9 (02) :235-248

[10] GENERAL PROCEDURE FOR BASE-PROMOTED HYDROLYSIS OF HINDERED ESTERS AT AMBIENT-TEMPERATURES [J].

GASSMAN, PG ;

SCHENK, WN .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (05) :918-920

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