Catalytic asymmetric cyclopropanation of heteroaryldiazoacetates

被引:91
作者
Davies, HML [1 ]
Townsend, RJ [1 ]
机构
[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
关键词
D O I
10.1021/jo015617t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rh-2(S-DOSP)(4)-catalyzed decomposition of heteroaryldiazoacetates in the presence of styrene results in highly diastereoselective and enantioselective cyclopropanations. Heteroaryldiazoacetates containing both electron-rich and electron-deficient heterocycles, such as thiophene, furan, pyridine, indole, oxazole, isoxazole, and benzoxazole, are effective in this chemistry. These studies broaden the range of diazo compounds containing both electron-withdrawing and electron-donating groups, which undergo highly diastereoselective cyclopropanations.
引用
收藏
页码:6595 / 6603
页数:9
相关论文
共 56 条
[1]   TOTAL SYNTHESIS OF 3-(5-TETRAZOLYL)CARBAPENEMS [J].
ANDRUS, A ;
HECK, JV ;
CHRISTENSEN, BG ;
PARTRIDGE, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (06) :1808-1811
[2]  
ASSMANN L, 1989, HETEROCYCLES, V29, P1003
[3]   SYNTHESIS OF AN OXEPINO[2,3-D]ISOXAZOLE SYSTEM [J].
ASSMANN, L ;
DEBAERDEMAEKER, T ;
FRIEDRICHSEN, W .
TETRAHEDRON LETTERS, 1991, 32 (09) :1161-1164
[4]   DIAZOTRANSFER REACTIONS WITH PARA-ACETAMIDOBENZENESULFONYL AZIDE [J].
BAUM, JS ;
SHOOK, DA ;
DAVIES, HML ;
SMITH, HD .
SYNTHETIC COMMUNICATIONS, 1987, 17 (14) :1709-1716
[5]  
BURGESS K, 1994, SYNLETT, P575
[6]   Asymmetric synthesis of 1-alkynylcyclopropane-1-carboxylates [J].
Davies, HML ;
Boebel, TA .
TETRAHEDRON LETTERS, 2000, 41 (43) :8189-8192
[7]   Stereoselectivity of methyl aryldiazoacetate cyclopropanations of 1,1-diarylethylene. Asymmetric synthesis of a cyclopropyl analogue of tamoxifen [J].
Davies, HML ;
Nagashima, T ;
Klino, JL .
ORGANIC LETTERS, 2000, 2 (06) :823-826
[8]   Catalytic asymmetric C-H activation of alkanes and tetrahydrofuran [J].
Davies, HML ;
Hansen, T ;
Churchill, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (13) :3063-3070
[9]   TANDEM CYCLOPROPANATION COPE REARRANGEMENT - A GENERAL-METHOD FOR THE CONSTRUCTION OF 7-MEMBERED RINGS [J].
DAVIES, HML .
TETRAHEDRON, 1993, 49 (24) :5203-5223
[10]   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