ENHANCEMENT OF ENANTIOCONTROL DIASTEREOCONTROL IN CATALYTIC INTRAMOLECULAR CYCLOPROPANATION AND CARBON-HYDROGEN INSERTION REACTIONS OF DIAZOACETATES WITH RH-2(4S-MPPIM)(4)

被引：73
作者：
DOYLE, MP
ZHOU, QL
DYATKIN, AB
RUPPAR, DA
机构：
[1] Department of Chemistry, Trinity University, San Antonio
来源：
TETRAHEDRON LETTERS | 1995年 / 36卷 / 42期
关键词：
D O I：
10.1016/0040-4039(95)01561-U
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Dirhodium(II) tetrakis[methyl 1-(3-phenylpropanoyl)imidazolidin-2-one-4(S)-carboxylate], Rh-2(4S-MPPIM)(4), provides significant enhancement in enantiocontrol for intramolecular cyclopropanation reactions of allylic diazoacetates and optimal enantiocontrol/diastereocontrol for intramolecular C-H insertion reactions of secondary alkyl diazoacetates.
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页码：7579 / 7582
页数：4
相关论文
共 12 条
[1]  
DOYLE MP, 1995, RECL TRAV CHIM PAY B, V114, P163
[2]   ASYMMETRIC-SYNTHESIS OF LACTONES WITH HIGH ENANTIOSELECTIVITY BY INTRAMOLECULAR CARBON HYDROGEN INSERTION REACTIONS OF ALKYL DIAZOACETATES CATALYZED BY CHIRAL RHODIUM(II) CARBOXAMIDES [J].
DOYLE, MP ;
VANOEVEREN, A ;
WESTRUM, LJ ;
PROTOPOPOVA, MN ;
CLAYTON, TW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) :8982-8984
[3]   HIGH ENANTIOSELECTIVITY IN THE INTRAMOLECULAR CYCLOPROPANATION OF ALLYL DIAZOACETATES USING A NOVEL RHODIUM(II) CATALYST [J].
DOYLE, MP ;
PIETERS, RJ ;
MARTIN, SF ;
AUSTIN, RE ;
OALMANN, CJ ;
MULLER, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (04) :1423-1424
[4]   DIASTEREOCONTROL FOR HIGHLY ENANTIOSELECTIVE CARBON-HYDROGEN INSERTION REACTIONS OF CYCLOALKYL DIAZOACETATES [J].
DOYLE, MP ;
DYATKIN, AB ;
ROOS, GHP ;
CANAS, F ;
PIERSON, DA ;
VANBASTEN, A ;
MULLER, P ;
POLLEUX, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (10) :4507-4508
[5]   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
[6]   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
[7]   SYNTHESIS OF 2-DEOXYXYLOLACTONE FROM GLYCEROL DERIVATIVES VIA HIGHLY ENANTIOSELECTIVE CARBON-HYDROGEN INSERTION REACTIONS [J].
DOYLE, MP ;
DYATKIN, AB ;
TEDROW, JS .
TETRAHEDRON LETTERS, 1994, 35 (23) :3853-3856
[8]   ENANTIOSELECTIVE, RHODIUM CATALYZED INTRAMOLECULAR CYCLOPROPANATIONS OF HOMOALLYTIC DIAZOACETATES [J].
MARTIN, SF ;
OALMANN, CJ ;
LIRAS, S .
TETRAHEDRON LETTERS, 1992, 33 (45) :6727-6730
[9]   CYCLOPROPANES AS CONFORMATIONALLY RESTRICTED PEPTIDE ISOSTERES - DESIGN AND SYNTHESIS OF NOVEL COLLAGENASE INHIBITORS [J].
MARTIN, SF ;
OALMANN, CJ ;
LIRAS, S .
TETRAHEDRON, 1993, 49 (17) :3521-3532
[10]  
MARTIN SF, 1991, J MED CHEM, V35, P1710
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