Synthesis of chiral dendrimers with a hydrocarbon backbone and application to the catalytic enantioselective addition of dialkylzincs to aldehydes

被引:44
作者
Sato, I [1 ]
Shibata, T [1 ]
Ohtake, K [1 ]
Kodaka, R [1 ]
Hirokawa, Y [1 ]
Shirai, N [1 ]
Soai, K [1 ]
机构
[1] Tokyo Univ Sci, Fac Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 1628601, Japan
关键词
asymmetric synthesis; catalysts; dendrimers; enantioselection;
D O I
10.1016/S0040-4039(00)00365-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral dendrimers with three or six beta-amino alcohols on hyperbranched hydrocarbon chain-ends were synthesized. These macromolecules can act as chiral catalysts for the enantioselective addition of dialkylzincs to aldehydes. The corresponding secondary alcohols are obtained in high enantiomeric excess (up to 86% e.e.). (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3123 / 3126
页数:4
相关论文
共 32 条
[1]  
Bolm C, 1996, SYNLETT, P387
[2]   About dendrimers: Structure, physical properties, and applications [J].
Bosman, AW ;
Janssen, HM ;
Meijer, EW .
CHEMICAL REVIEWS, 1999, 99 (07) :1665-1688
[3]   ENANTIOSELECTIVE CATALYSIS, .90. OPTICALLY-ACTIVE NITROGEN LIGANDS WITH DENDRIMERIC STRUCTURE [J].
BRUNNER, H ;
ALTMANN, S .
CHEMISCHE BERICHTE, 1994, 127 (11) :2285-2296
[4]  
Fischer M, 1999, ANGEW CHEM INT EDIT, V38, P885, DOI 10.1002/(SICI)1521-3773(19990401)38:7<884::AID-ANIE884>3.0.CO
[5]  
2-K
[6]   Synthesis and catalytic application of amino acid based dendritic macromolecules [J].
Gossage, RA ;
Jastrzebski, JTBH ;
van Ameijde, J ;
Mulders, SJE ;
Brouwer, AJ ;
Liskamp, RMJ ;
van Koten, G .
TETRAHEDRON LETTERS, 1999, 40 (07) :1413-1416
[7]   An alternative synthetic approach toward dendritic macromolecules:: Novel benzene-core dendrimers via alkyne cyclotrimerization [J].
Hecht, S ;
Fréchet, JMJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (16) :4084-4085
[8]   Structurally rigid and optically active dendrimers [J].
Hu, QS ;
Pugh, V ;
Sabat, M ;
Pu, L .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (20) :7528-7536
[9]  
ISSBERNER J, 1994, ANGEW CHEM INT EDIT, V33, P2413
[10]   NEW SOLID-PHASE CATALYSTS FOR ASYMMETRIC-SYNTHESIS - CROSS-LINKED POLYMERS CONTAINING A CHIRAL SHIFF BASE ZINC COMPLEX [J].
ITSUNO, S ;
SAKURAI, Y ;
ITO, K ;
MARUYAMA, T ;
NAKAHAMA, S ;
FRECHET, JMJ .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :304-310