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.
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收藏
页码:8075 / 8090
页数:16
相关论文
共 39 条
[21]  
KRUMPOLC M, 1981, ROCEK ORGANIC SYNTHE, V60, P20
[22]  
LERIVERE.P, 1968, B SOC CHIM FR, P2630
[23]   GAMMA-CHLOROBUTYRALDEHYDE AND ITS DIETHYL ACETAL [J].
LOFTFIELD, RB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (03) :1365-1366
[24]  
MARCH J, 1992, ADV ORG CHEM, P329
[25]  
MARIELLA RP, 1963, ORG SYNTH, V4, P288
[26]   SYNTHESIS OF POTENTIAL HYPNOTICS [J].
NEDENSKOV, P ;
TAUB, W ;
GINSBURG, D .
ACTA CHEMICA SCANDINAVICA, 1958, 12 (07) :1405-1410
[27]   A MILD AND EFFICIENT ROUTE TO SCHIFF-BASE DERIVATIVES OF AMINO-ACIDS [J].
ODONNELL, MJ ;
POLT, RL .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (13) :2663-2666
[28]  
PERKIN WH, 1887, J CHEM SOC, V51, P1
[29]  
PERKIN WH, 1892, J CHEM SOC, V61, P36
[30]  
RASMUSSEN JK, 1977, SYNTHESIS-STUTTGART, P91