Alkylation of magnesium enamide with alkyl chlorides and fluorides

被引:36
作者
Hatakeyama, T [1 ]
Ito, S [1 ]
Nakamura, M [1 ]
Nakamura, B [1 ]
机构
[1] Univ Tokyo, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan
关键词
D O I
10.1021/ja055306q
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A magnesium enamide derived from N-2-(N′,N′-diethylamino)ethyl imine reacts with a primary and secondary alkyl chloride or a primary alkyl fluoride to give an α-alkylated ketone in good to excellent yield after hydrolysis. The reaction takes place with a high level of inversion of stereochemistry at the electrophilic carbon center and will be useful for production of optically active compounds. Copyright © 2005 American Chemical Society.
引用
收藏
页码:14192 / 14193
页数:2
相关论文
共 18 条
[1]  
Caine D., 1991, Comprehensive Organic Synthesis, V3, P1
[2]  
Corey E. J., 1976, TETRAHEDRON LETT, V17, P7
[3]   THE RACEMISATION OF (-)-1-PHENYLETHYL CHLORIDE BY STANNIC CHLORIDE IN CARBON TETRACHLORIDE AND ITS BEARING ON THE CATIONIC POLYMERISATION OF STYRENE [J].
HEALD, K ;
WILLIAMS, G .
JOURNAL OF THE CHEMICAL SOCIETY, 1954, (JAN) :362-366
[4]   CHEMISTRY OF CARBANIONS .19. ALKYLATION OF ENOLATES FROM UNSYMMETRICAL KETONES [J].
HOUSE, HO ;
GALL, M ;
OLMSTEAD, HD .
JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (16) :2361-&
[5]   FLUORIDE-MEDIATED REACTIONS OF ENOL SILYL ETHERS - REGIOSPECIFIC MONOALKYLATION OF KETONES [J].
KUWAJIMA, I ;
NAKAMURA, E ;
SHIMIZU, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (04) :1025-1030
[6]   QUATERNARY AMMONIUM ENOLATES AS SYNTHETIC INTERMEDIATES - REGIOSPECIFIC ALKYLATION REACTION OF KETONES [J].
KUWAJIMA, I ;
NAKAMURA, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (11) :3257-3258
[7]   α-alkylation of ketones by addition of zinc enamides to unactivated olefins [J].
Nakamura, M ;
Hatakeyama, T ;
Nakamura, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (38) :11820-11825
[8]   Enantioselective synthesis of α-substituted ketones by asymmetric addition of chiral zinc enamides to 1-alkenes [J].
Nakamura, M ;
Hatakeyama, T ;
Hara, K ;
Nakamura, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (21) :6362-6363
[9]  
PATERSON I, 1979, TETRAHEDRON LETT, P1519
[10]  
REETZ MT, 1979, TETRAHEDRON LETT, P4971