Bifunctional asymmetric catalysis:: A tandem nucleophile/Lewis acid promoted synthesis of β-lactams

被引:94
作者
France, S [1 ]
Wack, H [1 ]
Hafez, AM [1 ]
Taggi, AE [1 ]
Witsil, DR [1 ]
Lectka, T [1 ]
机构
[1] Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA
关键词
D O I
10.1021/ol025805l
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We describe a superior procedure for the catalytic, asymmetric synthesis of beta-lactams using a bifunctional catalyst system consisting of a chiral nucleophile and an achiral Lewis acid.
引用
收藏
页码:1603 / 1605
页数:3
相关论文
共 16 条
[1]   Rate acceleration of the Baylis-Hillman reaction in polar solvents (water and formamide). Dominant role of hydrogen bonding, not hydrophobic effects, is implicated [J].
Aggarwal, VK ;
Dean, DK ;
Mereu, A ;
Williams, R .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (02) :510-514
[2]   Advances in indium-catalysed organic synthesis [J].
Chauhan, KK ;
Frost, CG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (18) :3015-3019
[3]   A catalyst that plays multiple roles:: Asymmetric synthesis of β-substituted aspartic acid derivatives through a four-stage, one-pot procedure [J].
Dudding, T ;
Hafez, AM ;
Taggi, AE ;
Wagerle, TR ;
Lectka, T .
ORGANIC LETTERS, 2002, 4 (03) :387-390
[4]   Catalytic, enantioselective alkylation of α-amino esters:: The synthesis of nonnatural α-amino acid derivatives [J].
Ferraris, D ;
Young, B ;
Cox, C ;
Dudding, T ;
Drury, WJ ;
Ryzhkov, L ;
Taggi, AE ;
Lectka, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (01) :67-77
[5]  
Gröger H, 2001, CHEM-EUR J, V7, P5247
[6]   Reactive ketenes through a carbonate/amine shuttle deprotonation strategy:: Catalytic, enantioselective α-bromination of acid chlorides [J].
Hafez, AM ;
Taggi, AE ;
Wack, H ;
Esterbrook, J ;
Lectka, T .
ORGANIC LETTERS, 2001, 3 (13) :2049-2051
[7]   Asymmetric catalysis on sequentially-linked columns [J].
Hafez, AM ;
Taggi, AE ;
Dudding, T ;
Lectka, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (44) :10853-10859
[8]   Column asymmetric catalysis for β-lactam synthesis [J].
Hafez, AM ;
Taggi, AE ;
Wack, H ;
Drury, WJ ;
Lectka, T .
ORGANIC LETTERS, 2000, 2 (25) :3963-3965
[9]   Mechanism of enantioselective Ti-catalyzed strecker reaction: Peptide-based metal complexes as bifunctional catalysts [J].
Josephsohn, NS ;
Kuntz, KW ;
Snapper, ML ;
Hoveyda, AH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (47) :11594-11599
[10]   Ambifunctional cooperative catalysts [J].
Rowlands, GJ .
TETRAHEDRON, 2001, 57 (10) :1865-1882