Two-fold amino acid-based chiral aminophosphine-oxazolines and use in asymmetric allylic alkylation

被引：23

作者：

Blanc, C ^{[1
]}

Hannedouche, J ^{[1
]}

Agbossou-Niedercorn, F ^{[1
]}

机构：

[1] ENSCL, Lab Catalyse Lille, CNRS, UMR 8010, F-59652 Villeneuve Dascq, France

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 34期

关键词：

D O I：

10.1016/S0040-4039(03)01561-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral aminophosphine-oxazoline ligands derived from two different amino acids (tetrahydroisoquinoline carboxylic acid and proline) have been synthesized and examined as chiral auxiliaries in asymmetric allylic alkylation of three substrates. Stereoisomers la and 2a are providing the highest enantio selectivities (up to 94% ee) in the allylation of diphenylpropenyl acetate. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：6469 / 6473

页数：5

共 41 条

[1] The aminophosphine-phosphinites and related ligands: synthesis, coordination chemistry and enantioselective catalysis [J].

Agbossou, F ;

Carpentier, JF ;

Hapiot, F ;

Suisse, I ;

Mortreux, A .

COORDINATION CHEMISTRY REVIEWS, 1998, 178 :1615-1645

[2]

AGBOSSOUNIEDERC.F, IN PRESS COORD CHEM

[3]

Alexakis A, 2001, SYNLETT, P1375

[4] PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC SUBSTITUTION - A LIGAND DESIGN INCORPORATING STERIC AND ELECTRONIC EFFECTS [J].

ALLEN, JV ;

COOTE, SJ ;

DAWSON, GJ ;

FROST, CG ;

MARTIN, CJ ;

WILLIAMS, JMJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (15) :2065-2072

[5]

[Anonymous], 1993, HDB ENANTIOSELECTIVE

[6]

Blankenstein J, 2001, ANGEW CHEM INT EDIT, V40, P4445, DOI 10.1002/1521-3773(20011203)40:23<4445::AID-ANIE4445>3.0.CO

[7]

2-V

[8]

Braunstein P, 2001, ANGEW CHEM INT EDIT, V40, P680, DOI 10.1002/1521-3773(20010216)40:4<680::AID-ANIE6800>3.0.CO

[9]

2-0

[10] Palladium complexes with a new hemilabile bis(oxazoline)phenylphosphonite ligand.: Characterization of an unprecedented chloro palladium(II)-(η1-allyl) complex [J].

Braunstein, P ;

Naud, F ;

Dedieu, A ;

Rohmer, MM ;

DeCian, A ;

Rettig, SJ .

ORGANOMETALLICS, 2001, 20 (14) :2966-2981

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