1,2-ASYMMETRIC CIS INDUCTION AND ITS APPLICATION TO THE ASYMMETRIC-SYNTHESIS OF PRECURSORS OF BETA-BRANCHED UNUSUAL AMINO-ACIDS

被引:20
作者
LI, G [1 ]
PATEL, D [1 ]
HRUBY, VJ [1 ]
机构
[1] UNIV ARIZONA,DEPT CHEM,TUCSON,AZ 85721
关键词
D O I
10.1016/0040-4039(94)85204-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new method for the asymmetric synthesis of key intermediates of unusual amino acids has been established by utilizing beta-carbon chirality for asymmetric induction in allylic-strained boron enolates.
引用
收藏
页码:2301 / 2304
页数:4
相关论文
共 30 条
[1]   ASYMMETRIC-SYNTHESIS OF UNUSUAL AMINO-ACIDS - AN EFFICIENT SYNTHESIS OF OPTICALLY PURE ISOMERS OF BETA-METHYLPHENYLALANINE [J].
DHARANIPRAGADA, R ;
VANHULLE, K ;
BANNISTER, A ;
BEAR, S ;
KENNEDY, L ;
HRUBY, VJ .
TETRAHEDRON, 1992, 48 (23) :4733-4748
[2]   ASYMMETRIC HALOGENATION OF CHIRAL IMIDE ENOLATES - A GENERAL-APPROACH TO THE SYNTHESIS OF ENANTIOMERICALLY PURE ALPHA-AMINO-ACIDS [J].
EVANS, DA ;
ELLMAN, JA ;
DOROW, RL .
TETRAHEDRON LETTERS, 1987, 28 (11) :1123-1126
[3]   STEREOSELECTIVE AMINATION OF CHIRAL ENOLATES - A NEW APPROACH TO THE ASYMMETRIC-SYNTHESIS OF ALPHA-HYDRAZINO AND ALPHA-AMINO-ACID DERIVATIVES [J].
EVANS, DA ;
BRITTON, TC ;
DOROW, RL ;
DELLARIA, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) :6395-6397
[4]   THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS - ELECTROPHILIC AZIDATION OF CHIRAL IMIDE ENOLATES, A PRACTICAL APPROACH TO THE SYNTHESIS OF (R)-ALPHA-AZIDO AND (S)-ALPHA-AZIDO CARBOXYLIC-ACIDS [J].
EVANS, DA ;
BRITTON, TC ;
ELLMAN, JA ;
DOROW, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) :4011-4030
[5]  
EVANS DA, 1984, ASYMMETRIC SYNTHESIS, V3, P96
[6]  
HEATHCOCK CH, 1984, ASYMMETRIC SYNTHESIS, V3, P111
[7]   STRATEGIES IN THE DEVELOPMENT OF PEPTIDE ANTAGONISTS [J].
HRUBY, VJ .
PROGRESS IN BRAIN RESEARCH, 1992, 92 :215-224
[9]   TOPOGRAPHICALLY DESIGNED ANALOGS OF [D-PEN,D-PEN5]ENKEPHALIN [J].
HRUBY, VJ ;
TOTH, G ;
GEHRIG, CA ;
KAO, LF ;
KNAPP, R ;
LUI, GK ;
YAMAMURA, HI ;
KRAMER, TH ;
DAVIS, P ;
BURKS, TF .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (06) :1823-1830
[10]   CONFORMATIONAL AND TOPOGRAPHICAL CONSIDERATIONS IN THE DESIGN OF BIOLOGICALLY-ACTIVE PEPTIDES [J].
HRUBY, VJ .
BIOPOLYMERS, 1993, 33 (07) :1073-1082