Reaction of methylcerium reagent with tertiary amides: Synthesis of saturated and unsaturated ketones from tertiary amides

被引:37
作者
Kurosu, M [1 ]
Kishi, Y [1 ]
机构
[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(98)00959-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of CeCl3 . MeLi to tertiary amides has been studied. The reagent prepared from cerium(III) chloride and methyllithium at 0 degrees C adds cleanly to morpholine amides to give the corresponding methyl ketones. Even in the presence of a large excess of the reagent, no tertiary alcohol formation is observed, indicating that the tetrahedral intermediates are stable under the reaction conditions employed. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4793 / 4796
页数:4
相关论文
共 14 条
[1]   PALLADIUM-CATALYZED CARBONYLATION OF ENOL TRIFLATES - A NOVEL METHOD FOR ONE-CARBON HOMOLOGATION OF KETONES TO ALPHA,BETA-UNSATURATED CARBOXYLIC-ACID DERIVATIVES [J].
CACCHI, S ;
MORERA, E ;
ORTAR, G .
TETRAHEDRON LETTERS, 1985, 26 (08) :1109-1112
[2]   ADDITIONS OF ALKYLLANTHANUM TRIFLATES TO CARBONYL-COMPOUNDS - REACTIVE ORGANOMETALLIC NUCLEOPHILES [J].
COLLINS, S ;
HONG, YP ;
HOOVER, GJ ;
VEIT, JR .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3565-3568
[3]   ORGANOCERIUM ADDITIONS TO HYDRAZONES - EFFECTS OF REAGENT STOICHIOMETRY ON EFFICIENCY AND SELECTIVITY [J].
DENMARK, SE ;
EDWARDS, JP ;
NICAISE, O .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (03) :569-578
[4]   Anhydrous cerium(III) chloride - Effect of the drying process on activity and efficiency [J].
Dimitrov, V ;
Kostova, K ;
Genov, M .
TETRAHEDRON LETTERS, 1996, 37 (37) :6787-6790
[5]   ULTRASOUND ASSISTED PREPARATION OF ORGANOCERIUM REAGENTS [J].
GREEVES, N ;
LYFORD, L .
TETRAHEDRON LETTERS, 1992, 33 (33) :4759-4760
[6]   SYNTHETIC STUDIES TOWARDS BATRACHOTOXIN .1. A FURAN-BASED INTRAMOLECULAR DIELS-ALDER ROUTE TO CONSTRUCT THE A-D RING-SYSTEM [J].
GRINSTEINER, TJ ;
KISHI, Y .
TETRAHEDRON LETTERS, 1994, 35 (45) :8333-8336
[7]  
GRINSTEINER TJ, 1994, TETRAHEDRON LETT, V35, P8377
[8]   SELECTIVE 1,2-ADDITION OF ORGANOCERIUM(III) REAGENTS TO ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS [J].
IMAMOTO, T ;
SUGIURA, Y .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 285 (1-3) :C21-C23
[9]   ORGANOCERIUM REAGENTS - NUCLEOPHILIC-ADDITION TO EASILY ENOLIZABLE KETONES [J].
IMAMOTO, T ;
SUGIURA, Y ;
TAKIYAMA, N .
TETRAHEDRON LETTERS, 1984, 25 (38) :4233-4236
[10]   CARBONYL ADDITION-REACTIONS PROMOTED BY CERIUM REAGENTS [J].
IMAMOTO, T .
PURE AND APPLIED CHEMISTRY, 1990, 62 (04) :747-752