Development of a novel chiral spiro ligand bearing oxazoline

被引:38
作者
Kato, T [1 ]
Marubayashi, K [1 ]
Takizawa, S [1 ]
Sasai, H [1 ]
机构
[1] Osaka Univ, Inst Sci & Ind Res, Dept Chem, Osaka 5670047, Japan
关键词
D O I
10.1016/j.tetasy.2004.09.037
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The synthesis of bis(oxazoline) ligand 1 bearing a spiro skeleton is achieved via double ring-closing metathesis (RCM) of tetraene 2 and subsequent oxazoline ring formation using N-bromosuccinimide (NBS). The Cu-spiro bis(oxazoline) complexes prepared from 1 and Cu(OTf)(2) or Cu(OAc)(2) act efficiently as chiral catalysts for promoting carbonyl-ene reactions or Henry reactions with good enantiocontrol. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3693 / 3697
页数:5
相关论文
共 36 条
[1]   A new asymmetric Wacker-type cyclization and tandem cyclization promoted by Pd(II)-spiro bis(isoxazoline) catalyst [J].
Arai, MA ;
Kuraishi, M ;
Arai, T ;
Sasai, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (12) :2907-2908
[2]   Design and synthesis of the first spiro bis(isoxazoline) derivatives as asymmetric ligands [J].
Arai, MA ;
Arai, T ;
Sasai, H .
ORGANIC LETTERS, 1999, 1 (11) :1795-1797
[3]   THE SYNTHESIS OF A FUNGAL ISONITRILE ANTIBIOTIC VIA A NOVEL RADICAL-ADDITION ELIMINATION-REACTION [J].
BALDWIN, JE ;
KELLY, DR ;
ZIEGLER, CB .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (02) :133-134
[4]   Spirocycle assembly through selective tandem ring closing metathesis reactions [J].
Bassindale, MJ ;
Hamley, P ;
Leitner, A ;
Harrity, JPA .
TETRAHEDRON LETTERS, 1999, 40 (16) :3247-3250
[5]   Novel spiro phosphinite ligands and their application in homogeneous catalytic hydrogenation reactions [J].
Chan, ASC ;
Hu, WH ;
Pai, CC ;
Lau, CP ;
Jiang, YZ ;
Mi, AQ ;
Yan, M ;
Sun, J ;
Lou, RL ;
Deng, JG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (40) :9570-9571
[6]   Catalytic asymmetric oxidation of tert-butyl disulfide.: Synthesis of tert-butanesulfinamides, tert-butyl sulfoxides, and tert-butanesulfinimines [J].
Cogan, DA ;
Liu, GC ;
Kim, KJ ;
Backes, BJ ;
Ellman, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (32) :8011-8019
[7]   Asymmetric synthesis of chiral amines by highly diastereoselective 1,2-additions of organometallic reagents to N-tert-butanesulfinyl imines [J].
Cogan, DA ;
Liu, GC ;
Ellman, J .
TETRAHEDRON, 1999, 55 (29) :8883-8904
[8]   A new copper acetate-bis(oxazoline)-catalyzed, enantioselective Henry reaction [J].
Evans, DA ;
Seidel, D ;
Rueping, M ;
Lam, HW ;
Shaw, JT ;
Downey, CW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (42) :12692-12693
[9]   C2-symmetric chiral bis(oxazoline)-metal complexes in catalytic asymmetric synthesis [J].
Ghosh, AK ;
Packiarajan, M ;
Cappiello, J .
TETRAHEDRON-ASYMMETRY, 1998, 9 (01) :1-45
[10]   NEIGHBORING GROUPS IN ADDITION .5. THE BENZAMIDO GROUP IN 3-BENZAMIDOPROPENE [J].
GOODMAN, L ;
WINSTEIN, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (17) :4788-4792