Asymmetric synthesis of 1-alkynylcyclopropane-1-carboxylates

被引:43
作者
Davies, HML [1 ]
Boebel, TA [1 ]
机构
[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
基金
美国国家科学基金会;
关键词
D O I
10.1016/S0040-4039(00)01453-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dirhodium tetrakis(S-(N-dodecylbenzenesulfonyl)prolinate)(Rh2S-DOSP4) catalyzed decomposition of methyl alkynyldiazoacetates in the presence of alkenes results in highly diastereoselective and enantioselective cyclopropanations. (C) 2000 Published by Elsevier Science Ltd.
引用
收藏
页码:8189 / 8192
页数:4
相关论文
共 15 条
[1]  
Davies H. M. L., 1997, ALDRICHIM ACTA, V30, P107
[2]  
Davies H.M. L., 1991, ORG SYNTH, V70, P93
[3]   Asymmetric cyclopropanations by rhodium(II) N-(arylsulfonyl)prolinate catalyzed decomposition of vinyldiazomethanes in the presence of alkenes. Practical enantioselective synthesis of the four stereoisomers of 2-phenylcyclopropan-1-amino acid [J].
Davies, HML ;
Bruzinski, PR ;
Lake, DH ;
Kong, N ;
Fall, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (29) :6897-6907
[4]   Effect of rhodium carbenoid structure on cyclopropanation chemoselectivity [J].
Davies, HML ;
Panaro, SA .
TETRAHEDRON, 2000, 56 (28) :4871-4880
[5]   Effect of catalyst on the diastereoselectivity of methyl phenyldiazoacetate cyclopropanations [J].
Davies, HML ;
Rusiniak, L .
TETRAHEDRON LETTERS, 1998, 39 (48) :8811-8812
[6]   STEREOSELECTIVE CYCLOPROPANATIONS WITH VINYLCARBENOIDS [J].
DAVIES, HML ;
CLARK, TJ ;
CHURCH, LA .
TETRAHEDRON LETTERS, 1989, 30 (38) :5057-5060
[7]  
DAVIES HML, 1993, HETEROCYCLES, V35, P385
[8]   Effect of diazoalkane structure on the stereoselectivity of rhodium(II) (S)-N-(arylsulfonyl)prolinate catalyzed cyclopropanations [J].
Davies, HML ;
Bruzinski, PR ;
Fall, MJ .
TETRAHEDRON LETTERS, 1996, 37 (24) :4133-4136
[9]  
Doyle M. P., 1998, MODERN CATALYTIC MET, P163
[10]   Chiral catalysts for enantioselective intermolecular cyclopropanation reactions with methyl phenyldiazoacetate. Origin of the solvent effect in reactions catalyzed by homochiral dirhodium(II) prolinates [J].
Doyle, MP ;
Zhou, QL ;
Charnsangavej, C ;
Longoria, MA ;
McKervey, MA ;
Garcia, CF .
TETRAHEDRON LETTERS, 1996, 37 (24) :4129-4132