ENANTIOSELECTIVE CATALYTIC INTRAMOLECULAR CYCLOPROPANATION OF ALLYLIC ALPHA-DIAZOPROPIONATES OPTIMIZED WITH DIRHODIUM(II) TETRAKIS[METHYL 2-OXAZOLIDINONE-4(S OR R)CARBOXYLATE]

被引:28
作者
DOYLE, MP
ZHOU, QL
机构
[1] Department of Chemistry, Trinity University, San Antonio
关键词
D O I
10.1016/0957-4166(95)00289-2
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
High enantiocontrol, up to 85% ee, has been achieved in intramolecular cyclopropanation reactions of representative allylic alpha-diazopropionates with the catalytic uses of Rh-2(4S-MEOX)(4).
引用
收藏
页码:2157 / 2160
页数:4
相关论文
共 17 条
[1]   ENANTIOSELECTIVELY CATALYZED INTRAMOLECULAR CYCLOPROPANATIONS OF UNSATURATED DIAZO CARBONYL-COMPOUNDS [J].
DAUBEN, WG ;
HENDRICKS, RT ;
LUZZIO, MJ ;
NG, HP .
TETRAHEDRON LETTERS, 1990, 31 (48) :6969-6972
[2]  
DOYLE MP, 1995, RECL TRAV CHIM PAY B, V114, P163
[3]   DIRHODIUM(II) TETRAKIS(CARBOXAMIDATES) WITH CHIRAL LIGANDS - STRUCTURE AND SELECTIVITY IN CATALYTIC METAL CARBENE TRANSFORMATIONS [J].
DOYLE, MP ;
WINCHESTER, WR ;
HOORN, JAA ;
LYNCH, V ;
SIMONSEN, SH ;
GHOSH, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :9968-9978
[4]   ENANTIOSELECTIVE INTRAMOLECULAR CYCLOPROPANATIONS OF ALLYLIC AND HOMOALLYLIC DIAZOACETATES AND DIAZOACETAMIDES USING CHIRAL DIRHODIUM(II) CARBOXAMIDE CATALYSTS [J].
DOYLE, MP ;
AUSTIN, RE ;
BAILEY, AS ;
DWYER, MP ;
DYATKIN, AB ;
KALININ, AV ;
KWAN, MMY ;
LIRAS, S ;
OALMANN, CJ ;
PIETERS, RJ ;
PROTOPOPOVA, MN ;
RAAB, CE ;
ROOS, GHP ;
ZHOU, QL ;
MARTIN, SF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (21) :5763-5775
[5]  
DOYLE MP, 1993, CATALYTIC ASYMMETRIC
[6]   ENANTIOSELECTIVE INTRAMOLECULAR C-H INSERTION OF ALPHA-DIAZO BETA-KETO-ESTERS CATALYZED BY HOMOCHIRAL RHODIUM(II) CARBOXYLATES [J].
HASHIMOTO, S ;
WATANABE, N ;
IKEGAMI, S .
TETRAHEDRON LETTERS, 1990, 31 (36) :5173-5174
[7]   DOUBLE ASYMMETRIC INDUCTION IN INTRAMOLECULAR C-H INSERTION REACTIONS OF ALPHA-DIAZO BETA-KETO-ESTERS [J].
HASHIMOTO, S ;
WATANABE, N ;
KAWANO, K ;
IKEGAMI, S .
SYNTHETIC COMMUNICATIONS, 1994, 24 (22) :3277-3287
[8]   SYNTHESIS OF BETA-METHOXY ENONES VIA A NEW 2-CARBON EXTENSION OF CARBOXYLIC-ACIDS [J].
HUDLICKY, T ;
OLIVO, HF ;
NATCHUS, MG ;
UMPIERREZ, EF ;
PANDOLFI, E ;
VOLONTERIO, C .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15) :4767-4770
[9]   ASYMMETRIC-SYNTHESIS IN CARBON CARBON BOND FORMING REACTIONS OF ALPHA-DIAZOKETONES CATALYZED BY HOMOCHIRAL RHODIUM(II) CARBOXYLATES [J].
KENNEDY, M ;
MCKERVEY, MA ;
MAGUIRE, AR ;
ROOS, GHP .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (05) :361-362
[10]   ASYMMETRIC CATALYSIS IN INTRAMOLECULAR CYCLOPROPANATION [J].
KOSKINEN, AMP ;
HASSILA, H .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16) :4479-4480