The reductive coupling of tertiary amides to give enediamines using PhMe2SiLi

被引:19
作者
Fleming, I
Ghosh, U
Mack, SR
Clark, BP
机构
[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
[2] Eli Lilly & Co, Lilly Res Ctr Ltd, Windlesham GU20 6PH, Surrey, England
关键词
D O I
10.1039/a800648b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
PhMe2SiLi reacts with tertiary amides to give enediamines, which can be isolated in good yield when the alpha-carbon is branched; the enediamines can be hydrolysed more or less easily to alpha-amino ketones, isomerised from Z to E, oxidised to dienediamines and isomerised to amino enamines.
引用
收藏
页码:711 / 712
页数:2
相关论文
共 26 条
[1]  
BONINI BF, 1995, SYNTHESIS-STUTTGART, P92
[2]   CHEMISTRY OF SILYL THIOKETONES .7. SYNTHESIS, CYCLOADDITION AND OXIDATION OF CYCLOALKYL SILYL THIOKETONES AND DESILYLATION OF THE REACTION-PRODUCTS [J].
BONINI, BF ;
BUSI, F ;
DELAET, RC ;
MAZZANTI, G ;
THURING, JWJF ;
ZANI, P ;
ZWANENBURG, B .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (09) :1011-1018
[3]   SILYLATION OF IMIDOYL CHLORIDE - APPLICATION TO ACYLSILANE SYNTHESIS [J].
BOURGEOI.P .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1974, 76 (01) :C1-C3
[4]   NEW SYNTHESIS OF ACYLSILANES [J].
BOURGEOIS, P ;
DUNOGUES, J ;
DUFFAUT, N ;
LAPOUYAD.P .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1974, 80 (02) :C25-C26
[5]   ENAMINE CHEMISTRY .4. CYCLOADDITION REACTIONS OF ENAMINES DERIVED FROM ALDEHYDES + ACYCLIC KETONES [J].
BRANNOCK, KC ;
KELLY, CA ;
BURPITT, RD ;
BELL, A .
JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (04) :801-&
[6]   ENAMINE CHEMISTRY .V. CYCLOADDITION REACTIONS OF ENAMINES DERIVED FROM ALICYCLIC KETONES [J].
BRANNOCK, KC ;
BURPITT, RD ;
GOODLETT, VW ;
THWEATT, JG .
JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (04) :813-&
[7]  
BRAVOZHITIVITOV.DA, 1983, J ORGANOMET CHEM, V114, P51
[8]   PHOTOCHEMISTRY OF ACYLDISILANES [J].
BROOK, AG ;
BAUMEGGER, A ;
LOUGH, AJ .
ORGANOMETALLICS, 1992, 11 (01) :310-317
[9]   The reactions of phenyldimethylsilyllithium with nitriles [J].
Fleming, I ;
Solay, M ;
Stolwijk, F .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1996, 521 (1-2) :121-124
[10]   REACTION OF ENAMINES WITH ELECTROPHILIC OLEFINS . SYNTHESIS OF CYCLOBUTANES [J].
FLEMING, I ;
HARLEYMASON, J .
JOURNAL OF THE CHEMICAL SOCIETY, 1964, (JUN) :2165-&