THE FIRST DIRECT PREPARATION OF CHIRAL FUNCTIONALIZED KETONES AND THEIR SYNTHETIC USES

被引:58
作者
BARLUENGA, J
BARAGANA, B
ALONSO, A
CONCELLON, JM
机构
关键词
D O I
10.1039/c39940000969
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Almost enantiomerically pure halogenated alpha-hydroxy and alpha-amino ketones can be prepared from O-protected lactates and tribenzylated alanine, respectively; whilst amino ketones 3g have also been transformed into the amino epoxide 7 with high diastereoselectivity.
引用
收藏
页码:969 / 970
页数:2
相关论文
共 11 条
[1]   CHIRAL [O-16,O-17,O-18]PHOSPHATE MONO-ESTERS - ASYMMETRIC SYNTHESIS AND STEREOCHEMICAL ANALYSIS OF [1(R)-O-16,O-17,O-18]PHOSPHO-(S)-PROPANE-1,2-DIOL [J].
ABBOTT, SJ ;
JONES, SR ;
WEINMAN, SA ;
BOCKHOFF, FM ;
MCLAFFERTY, FW ;
KNOWLES, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (15) :4323-4332
[2]   HIGH DIASTEREOFACE SELECTION IN AN ESTER ENOLATE ADDITION TO ALPHA-ALKOXY ALDEHYDES - STEREOSELECTIVE SYNTHESIS OF ALPHA-METHYLENE-BETA-HYDROXY-GAMMA-ALKOXY ESTERS [J].
BANFI, L ;
BERNARDI, A ;
COLOMBO, L ;
GENNARI, C ;
SCOLASTICO, C .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (20) :3784-3790
[3]   A SIMPLE AND UNAMBIGUOUS SYNTHESIS OF ALPHA,ALPHA-DIHALOGENO AND ALPHA,ALPHA'-DIHALOGENO KETONES [J].
BARLUENGA, J ;
LLAVONA, L ;
CONCELLON, JM ;
YUS, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (02) :297-300
[4]  
Chaudhury S. C., 1979, TETRAHEDRON LETT, V20, P99
[5]   A STEREOCONTROLLED SYNTHESIS OF HYDROXYETHYLENE DIPEPTIDE ISOSTERES USING NOVEL, CHIRAL AMINOALKYL EPOXIDES AND GAMMA-(AMINOALKYL) GAMMA-LACTONES [J].
EVANS, BE ;
RITTLE, KE ;
HOMNICK, CF ;
SPRINGER, JP ;
HIRSHFIELD, J ;
VEBER, DF .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (23) :4615-4625
[6]   HIGHLY DIASTEREOSELECTIVE ALDOL REACTIONS OF CHIRAL METHYL KETONES [J].
LAGU, BR ;
CRANE, HM ;
LIOTTA, DC .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16) :4191-4193
[7]   A SYNTHESIS OF PROTECTED AMINOALKYL EPOXIDES FROM ALPHA-AMINO-ACIDS [J].
LULY, JR ;
DELLARIA, JF ;
PLATTNER, JJ ;
SODERQUIST, JL ;
YI, N .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (08) :1487-1492
[8]   STEREOSELECTIVE SYNTHESIS OF BETA-AMINO ALCOHOLS FROM OPTICALLY-ACTIVE ALPHA-AMINO-ACIDS [J].
REETZ, MT ;
DREWES, MW ;
SCHMITZ, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (11) :1141-1143
[9]   PROTECTIVE GROUP TUNING IN THE STEREOSELECTIVE CONVERSION OF ALPHA-AMINO ALDEHYDES INTO AMINOALKYL EPOXIDES [J].
REETZ, MT ;
BINDER, J .
TETRAHEDRON LETTERS, 1989, 30 (40) :5425-5428
[10]   NEW APPROACHES TO THE USE OF AMINO-ACIDS AS CHIRAL BUILDING-BLOCKS IN ORGANIC-SYNTHESIS [J].
REETZ, MT .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (12) :1531-1546