Regioselective synthesis of α,α-dialkylcyclopentanones from 1-hydroxycyclobutanecarboxylic acid or from O-protected cyclobutanone cyanohydrin.

被引:6
作者
Estieu, K [1 ]
Ollivier, J [1 ]
Salaün, J [1 ]
机构
[1] Univ Paris Sud, Inst Chim Mol Orsay, Lab Carbocycles, CNRS, F-91405 Orsay, France
关键词
D O I
10.1016/S0040-4020(98)00448-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1-(1-Hydroxyalkyl)cylobutanols 4a-f, readily available either from 1-hydroxycyclobutane carboxylic acid or from O-protected cyclobutanone cyanohydrin, appeared the most suitable precursors for a regioselective synthesis of cyclopentanones alpha,alpha-disubstituted with various similar or different alkyl, alkenyl, aryl or cycloalkyl groups. The key steps consist of acid or Grignard reagent induced C-4 --> C-5 ring expansions. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8075 / 8090
页数:16
相关论文
共 39 条
[1]  
BARNIER JP, 1975, B SOC CHIM FR II-CH, P1654
[2]   THE SYNTHESIS OF SUBSTANCES RELATED TO THE STEROLS .44. DL-CIS-EQUILENIN [J].
BIRCH, AJ ;
JAEGER, R ;
ROBINSON, R .
JOURNAL OF THE CHEMICAL SOCIETY, 1945, :582-586
[3]  
BNAERJEE UK, 1983, TTERAHEDRON LETT, P4625
[4]   CYCLOBUTANE RING CONTRACTIONS NOT INVOLVING CARBONIUM-IONS [J].
CONIA, JM ;
SALAUN, JR .
ACCOUNTS OF CHEMICAL RESEARCH, 1972, 5 (01) :33-+
[5]  
CONLEY RT, 1962, RECL TRAV CHIM PAY B, V81, P198
[6]  
CRIEGEE R, 1956, LIEBIGS ANN CHEM, V599, P81
[7]  
DANGELO J, 1975, B SOC CHIM FR II-CH, P333
[8]   SYNTHESES OF THE PRINCIPAL BREAD FLAVOR COMPONENT, 6-ACETYL-1,2,3,4-TETRAHYDROPYRIDINE, AND ACETAL PROTECTED PRECURSORS [J].
DEKIMPE, N ;
STEVENS, C .
TETRAHEDRON, 1995, 51 (08) :2387-2402
[9]  
DEMJANOW NJ, 1922, CHEM BER, V55, P2737
[10]   STEREOCHEMICAL EFFECTS IN THE GAS-PHASE PINACOL REARRANGEMENT OF CIS-1,2-DIMETHYLCYCLOPENTANE-1,2-DIOL AND TRANS-1,2-DIMETHYLCYCLOPENTANE-1,2-DIOL [J].
DEPETRIS, G ;
GIACOMELLO, P ;
PICOTTI, T ;
PIZZABIOCCA, A ;
RENZI, G ;
SPERANZA, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (24) :7491-7495