ONE-POT SYNTHESIS OF ALPHA,BETA-UNSATURATED KETONES FROM TERT-BUTYLDIMETHYLSILYLDIBROMOMETHANE AND 2 DIFFERENT ALDEHYDES

被引:8
作者
SHINOKUBO, H [1 ]
OSHIMA, K [1 ]
UTIMOTO, K [1 ]
机构
[1] KYOTO UNIV,FAC ENGN,DIV MAT CHEM,SAKYO KU,KYOTO 60601,JAPAN
关键词
D O I
10.1016/S0040-4039(00)73086-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An addition of benzaldehyde to an ethereal solution of tert-butyldimethylsilyldibromo-methyllithium provided alpha-bromo-alpha-silyl ketone. Further treatment of the alpha-bromo-alpha-silyl ketone with butyllithium afforded enolate which provided beta-hydroxy-alpha-silyl ketone upon treatment with aldehyde in ether. The enolate gave alpha,beta-unsaturated ketone or monosilyl ether of 2-acyl-1,3-diol in THF instead of ether.
引用
收藏
页码:3741 / 3744
页数:4
相关论文
共 15 条
[1]   A NEW METHOD FOR THE SYNTHESIS OF ALPHA-BROMOACYL SILANES VIA RING-OPENING OF 2-PHENYLSULFONYL-2-TRIMETHYLSILYLOXIRANES [J].
HEWKIN, CT ;
JACKSON, RFW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (12) :3103-3111
[2]  
KOBRICH G, 1972, TETRAHEDRON LETT, P4117
[3]   EFFICIENT METHOD FOR PREPARATION OF ACYLSILANE AND ALPHA-HALOACYLSILANE [J].
KUWAJIMA, I ;
ABE, T ;
MINAMI, N .
CHEMISTRY LETTERS, 1976, (09) :993-994
[4]  
LARCHEVEQUE M, 1981, J CHEM SOC CHEM COMM, P877, DOI 10.1039/c39810000877
[5]   A STEREOSELECTIVE, 2-STEP PREPARATION OF ALPHA-ALKYL-ALPHA,BETA-UNSATURATED ESTERS [J].
LARSON, GL ;
DEKAIFER, CF ;
SEDA, R ;
TORRES, LE ;
RAMIREZ, JR .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (18) :3385-3386
[6]   A REGIOSELECTIVE ENOLATE FORMATION OF TRIMETHYLSILYLMETHYL KETONES APPLICATION TO THE (E)-SELECTIVE SYNTHESIS OF ALPHA,BETA-UNSATURATED KETONES [J].
MATSUDA, I ;
OKADA, H ;
SATO, S ;
IZUMI, Y .
TETRAHEDRON LETTERS, 1984, 25 (35) :3879-3882
[7]  
PAGE PCB, 1990, TETRAHEDRON, V46, P2573
[8]  
SATO T, 1978, TETRAHEDRON LETT, P259
[9]   TERT-BUTYLDIMETHYLSILYLDICHLOROMETHYLLITHIUM AS A DICHLOROMETHYLENE DIANION SYNTHON - 1,3-REARRANGEMENT OF SILYL GROUP FROM CARBON TO OXIDE [J].
SHINOKUBO, H ;
MIURA, K ;
OSHIMA, K ;
UTIMOTO, K .
TETRAHEDRON LETTERS, 1993, 34 (12) :1951-1954
[10]   BETA-OXIDO CARBENOIDS AS SYNTHETIC INTERMEDIATES - FACILE RING ENLARGEMENT REACTION [J].
TAGUCHI, H ;
YAMAMOTO, H ;
NOZAKI, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (20) :6510-6511