REVERSAL OF DIASTEREOSELECTIVITY IN THE ADDITION OF C-NUCLEOPHILES TO N-TRIMETHYLSILYL IMINES VIA GRIGNARD DERIVED ORGANO COPPER-BORON TRIFLUORIDE REAGENTS

被引:18
作者
CAINELLI, G [1 ]
GIACOMINI, D [1 ]
PANUNZIO, M [1 ]
ZARANTONELLO, P [1 ]
机构
[1] CNR,CSFM,I-40126 BOLOGNA,ITALY
关键词
D O I
10.1016/0040-4039(93)88045-K
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The N-trimethylsilyl imines of O-protected alpha-hydroxy aldehydes react with RCuMgXI BF3 to give beta-amino alcohols with high anti diastereoselectivity.
引用
收藏
页码:7783 / 7786
页数:4
相关论文
共 28 条
[1]   BETA-LACTAMS FROM ESTER ENOLATES AND SILYLIMINES - ENANTIOSELECTIVE SYNTHESIS OF THE TRANS-CARBAPENEM ANTIBIOTICS (+)-PS-5 AND (+)-PS-6 [J].
ANDREOLI, P ;
CAINELLI, G ;
PANUNZIO, M ;
BANDINI, E ;
MARTELLI, G ;
SPUNTA, G .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (21) :5984-5990
[2]   BETA-LACTAMS FROM ESTER ENOLATES AND SILYLIMINES - AN ENANTIOSPECIFIC SYNTHESIS OF MONOCYCLIC BETA-LACTAMS [J].
ANDREOLI, P ;
BILLI, L ;
CAINELLI, G ;
PANUNZIO, M ;
BANDINI, E ;
MARTELLI, G ;
SPUNTA, G .
TETRAHEDRON, 1991, 47 (43) :9061-9070
[3]   STRUCTURAL AND ENERGETIC EVIDENCE FOR O-LI-N CHELATION IN A MODEL FOR ASYMMETRIC INDUCTION [J].
ARNETT, EM ;
NICHOLS, MA ;
MCPHAIL, AT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (19) :7059-7060
[4]   NEW COPPER CHEMISTRY .15. ORGANOCOPPER REAGENTS IN DIMETHYL SULFIDE [J].
BERTZ, SH ;
DABBAGH, G .
TETRAHEDRON, 1989, 45 (02) :425-434
[5]   SYNTHESIS OF OPTICALLY-ACTIVE ETHANOLAMINES [J].
BRUSSEE, J ;
DOFFERHOFF, F ;
KRUSE, CG ;
VANDERGEN, A .
TETRAHEDRON, 1990, 46 (05) :1653-1658
[6]   MAGNESIUM-ION MEDIATED STEREOSPECIFIC FORMATION OF N-SUBSTITUTED ETHANOLAMINES DURING REDUCTIVE AMINATION [J].
BRUSSEE, J ;
VANBENTHEM, RATM ;
KRUSE, CG ;
VANDERGEN, A .
TETRAHEDRON-ASYMMETRY, 1990, 1 (03) :163-166
[7]   N-METALLO-IMINES - A NEW APPROACH TO ALPHA-AMINO ALCOHOLS FROM CYANOHYDRINS [J].
CAINELLI, G ;
MEZZINA, E ;
PANUNZIO, M .
TETRAHEDRON LETTERS, 1990, 31 (24) :3481-3484
[8]   BETA-LACTAMS FROM ESTER ENOLATES AND SILYLIMINES - ENANTIOSELECTIVE SYNTHESIS OF (+)-PS-5 [J].
CAINELLI, G ;
PANUNZIO, M ;
GIACOMINI, D ;
MARTELLI, G ;
SPUNTA, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) :6879-6880
[9]  
CAINELLI G, 1991, TETRAHEDRON LETT, V33, P2967
[10]   CHELATES AS INTERMEDIATES IN NUCLEOPHILIC ADDITIONS TO ALKOXY KETONES ACCORDING TO CRAM RULE (CYCLIC MODEL) [J].
CHEN, XN ;
HORTELANO, ER ;
ELIEL, EL ;
FRYE, SV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) :1778-1784