Highly regio-, diastereo-, and enantioselective C-H insertions of methyl aryldiazoacetates into cyclic N-BOC-protected amines.: Asymmetric synthesis of novel C2-symmetric amines and threo-methylphenidate

被引:142
作者
Davies, HML [1 ]
Hansen, T [1 ]
Hopper, DW [1 ]
Panaro, SA [1 ]
机构
[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
关键词
D O I
10.1021/ja9910715
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
引用
收藏
页码:6509 / 6510
页数:2
相关论文
共 26 条
[1]   RHODIUM ACETATE CATALYZES THE ADDITION OF CARBENOIDS ALPHA-OXYGENS TO ETHER OXYGENS [J].
ADAMS, J ;
POUPART, MA ;
GRENIER, L ;
SCHALLER, C ;
OUIMET, N ;
FRENETTE, R .
TETRAHEDRON LETTERS, 1989, 30 (14) :1749-1752
[2]  
AMBRAMOVITCH RA, 1965, J CHEM SOC CHEM COMM, P542
[3]   SELECTIVE INTERMOLECULAR CARBON-HYDROGEN BOND ACTIVATION BY SYNTHETIC METAL-COMPLEXES IN HOMOGENEOUS SOLUTION [J].
ARNDTSEN, BA ;
BERGMAN, RG ;
MOBLEY, TA ;
PETERSON, TH .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (03) :154-162
[4]   A stereoselective synthesis of dl-threo-methylphenidate:: Preparation and biological evaluation of novel analogues [J].
Axten, JM ;
Krim, L ;
Kung, HF ;
Winkler, JD .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9628-9629
[5]   trans-1,2-diaminocyclohexane derivatives as chiral reagents, scaffolds, and ligands for catalysis: Applications in asymmetric synthesis and molecular recognition [J].
Bennani, YL ;
Hanessian, S .
CHEMICAL REVIEWS, 1997, 97 (08) :3161-3195
[6]   HOMOLOGATION OF N-ALKANES USING DIAZOESTERS AND RHODIUM(III)PORPHYRINS - ENHANCED ATTACK ON PRIMARY C-H BONDS [J].
CALLOT, HJ ;
METZ, F .
TETRAHEDRON LETTERS, 1982, 23 (42) :4321-4324
[7]  
CALLOT HJ, 1985, NOUV J CHIM, V9, P167
[8]   Benzocarbapenems from indoles [J].
Coulton, S ;
Gilchrist, TL ;
Graham, K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (07) :1193-1202
[9]  
Davies H. M. L., 1997, ALDRICHIM ACTA, V30, P107
[10]   Asymmetric intermolecular carbenoid C-H insertions catalyzed by rhodium(II) (S)-N-(p-dodecylphenyl)sulfonylprolinate [J].
Davies, HML ;
Hansen, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (38) :9075-9076