UNUSUAL DIASTEREOFACIAL SELECTIVITY IN THE MICHAEL ADDITION-REACTIONS OF LITHIATED 2-AMINOACETATES AND 2-ACETAMIDES TO ALPHA, BETA-UNSATURATED CARBONYL-COMPOUNDS

被引:8
作者
KANEMASA, S [1 ]
NOMURA, M [1 ]
TAGUCHI, Y [1 ]
机构
[1] KYUSHU UNIV, INTERDISCIPLINARY GRAD SCH ENGN SCI, DEPT MOLEC SCI & TECHNOL, KASUGA, FUKUOKA 816, JAPAN
关键词
D O I
10.1246/cl.1992.1801
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Unusual diastereofacial selectivities are observed in the Michael addition reactions of lithiated aminoacetates and -acetamides to alpha,beta-unsaturated carbonyl acceptors. Lithiated (methylamino)acetates and -acetamides show opposite anti- and syn-selectivities, respectively, while lithiated (dialkylamino)acetates and -acetamides are both highly syn-selective.
引用
收藏
页码:1801 / 1804
页数:4
相关论文
共 29 条
[21]  
OARE DA, 1989, TOPICS STEREOCHEMIST
[22]  
PETTIG D, 1988, SYNTHESIS-STUTTGART, P173
[23]  
SCHOLLKOPF U, 1986, SYNTHESIS-STUTTGART, P737
[24]   ASYMMETRIC-SYNTHESIS VIA HETEROCYCLIC INTERMEDIATES .41. ENANTIO-SELECTIVE AND DIASTEREOSELECTIVE SYNTHESIS OF METHYL (2R)-2-AMINO-5-OXOCARBOXYLATES FROM ENONES AND BISLACTIM-ETHER CUPRATES [J].
SCHOLLKOPF, U ;
PETTIG, D ;
SCHULZE, E ;
KLINGE, M ;
EGERT, E ;
BENECKE, B ;
NOLTEMEYER, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (09) :1194-1195
[25]   CONSTRUCTION OF CONTIGUOUS QUATERNARY AND TERTIARY CARBON CENTERS VIA THE ASYMMETRIC MICHAEL REACTION [J].
TOMIOKA, K ;
YASUDA, K ;
KOGA, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (18) :1345-1346
[26]  
VITEVA L, 1990, J CHEM RES S, P323
[27]   A DIASTEREOSELECTIVE AND ENANTIOSELECTIVE MICHAEL ADDITION OF CHIRAL AMIDE ENOLATES TO PI,BETA-UNSATURATED ESTERS - A STEREOSELECTIVE SYNTHESIS OF (+)-DEHYDROIRIDODIOL AND (-)-ISODEHYDROIRIDODIOL [J].
YAMAGUCHI, M ;
HASEBE, K ;
TANAKA, S ;
MINAMI, T .
TETRAHEDRON LETTERS, 1986, 27 (08) :959-962
[28]   THREO-SELECTIVE MICHAEL ADDITION OF N,N-DIBENZYLGLYCINATE AND ALANINATE ENOLATES TO ALPHA,BETA-UNSATURATED ESTERS - A CONCISE AND STEREOSELECTIVE SYNTHESIS OF (+/-)-CCG-II [J].
YAMAGUCHI, M ;
TORISU, K ;
MINAMI, T .
CHEMISTRY LETTERS, 1990, (03) :377-380
[29]   ASYMMETRIC MICHAEL ADDITION OF THE N-ALKYLIDENE DERIVATIVE OF AN ALPHA-AMINO ESTER TO METHYL (E)-3-((3R,7AS)-2-PHENYLPERHYDROPYRROLO(1,2-C)IMIDAZOL-3-YL)PROPENOATE [J].
YAMAMOTO, H ;
KANEMASA, S ;
WADA, E .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (09) :2739-2743