Intramolecular cyclopropanation reactions en route to novel P-heterocycles

被引:22
作者
Hanson, PR [1 ]
Sprott, KT [1 ]
Wrobleski, AD [1 ]
机构
[1] Univ Kansas, Dept Chem, Lawrence, KS 66045 USA
关键词
D O I
10.1016/S0040-4039(99)00023-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first examples of intramolecular cyclopropanation reactions on a phosphonate template catalyzed by Rh-2(OAc)(4) are described. These reactions proceed in excellent yield and give mixtures of the P-heterocycles cis-2a-d and trans-2a-d with moderate levels of diastereoselectivity. The diastereoselectivity of this transformation is dependent upon the size of the alkyl group R contained in the alkyl alpha-diazodiallylphosphonoacetate starting materials 1a-d. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1455 / 1458
页数:4
相关论文
共 27 条
[1]   TANDEM WOLFF REARRANGEMENT TERT-AMINO-EFFECT SEQUENCE - SYNTHESIS OF 2-OXOINDOLLINIUM ENOLATE AND 1H-2-BENZOPYRANE DERIVATIVES [J].
CHANTEGREL, B ;
DESHAYES, C ;
FAURE, R .
TETRAHEDRON LETTERS, 1995, 36 (43) :7859-7862
[2]   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
[3]   STEREOSELECTIVE CYCLOPROPANATIONS WITH VINYLCARBENOIDS [J].
DAVIES, HML ;
CLARK, TJ ;
CHURCH, LA .
TETRAHEDRON LETTERS, 1989, 30 (38) :5057-5060
[4]   ORGANIC PHOSPHORUS-COMPOUNDS .78. MANUFACTURE AND PROPERTIES OF N-PHOSPHONOMETHYLGLYCINE DERIVATIVES [J].
DIEL, PJ ;
MAIER, L .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1984, 20 (03) :313-321
[5]  
Doyle M. P., 1998, MODERN CATALYTIC MET
[6]   Recent advances in asymmetric catalytic metal carbene transformations [J].
Doyle, MP ;
Forbes, DC .
CHEMICAL REVIEWS, 1998, 98 (02) :911-935
[7]   CORRELATIONS BETWEEN CATALYTIC REACTIONS OF DIAZO-COMPOUNDS AND STOICHIOMETRIC REACTIONS OF TRANSITION-METAL CARBENES WITH ALKENES - MECHANISM OF THE CYCLOPROPANATION REACTION [J].
DOYLE, MP ;
GRIFFIN, JH ;
BAGHERI, V ;
DOROW, RL .
ORGANOMETALLICS, 1984, 3 (01) :53-61
[8]   STEREOSELECTIVITY OF CATALYTIC CYCLOPROPANATION REACTIONS - CATALYST DEPENDENCE IN REACTIONS OF ETHYL DIAZOACETATE WITH ALKENES [J].
DOYLE, MP ;
DOROW, RL ;
BUHRO, WE ;
GRIFFIN, JH ;
TAMBLYN, WH ;
TRUDELL, ML .
ORGANOMETALLICS, 1984, 3 (01) :44-52
[9]   MACROCYCLIC LACTONES FROM DIRHODIUM(II)-CATALYZED INTRAMOLECULAR CYCLOPROPANATION AND CARBON-HYDROGEN INSERTION [J].
DOYLE, MP ;
PROTOPOPOVA, MN ;
POULTER, CD ;
ROGERS, DH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (27) :7281-7282
[10]   HIGHLY SELECTIVE ENANTIOMER DIFFERENTIATION IN INTRAMOLECULAR CYCLOPROPANATION REACTIONS OF RACEMIC SECONDARY ALLYLIC DIAZOACETATES [J].
DOYLE, MP ;
DYATKIN, AB ;
KALININ, AV ;
RUPPAR, DA ;
MARTIN, SF ;
SPALLER, MR ;
LIRAS, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (44) :11021-11022