AN ENHANCEMENT OF ENANTIOSELECTIVITY IN CHIRAL LITHIUM AMIDE DEPROTONATIONS DUE TO LITHIUM-CHLORIDE

被引:108
作者
BUNN, BJ [1 ]
SIMPKINS, NS [1 ]
机构
[1] UNIV NOTTINGHAM,DEPT CHEM,UNIV PK,NOTTINGHAM NG7 2RD,ENGLAND
关键词
D O I
10.1021/jo00055a001
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Substantial improvements in the enantiomeric excess of products obtained from chiral base-mediated reactions of prochiral ketones under external quench (EQ) conditions are observed if the deprotonation is carried out in the presence of added LiCl.
引用
收藏
页码:533 / 534
页数:2
相关论文
共 17 条
[1]   ASYMMETRIC DEPROTONATION OF PROCHIRAL KETONES USING CHIRAL LITHIUM AMIDE BASES [J].
CAIN, CM ;
COUSINS, RPC ;
COUMBARIDES, G ;
SIMPKINS, NS .
TETRAHEDRON, 1990, 46 (02) :523-544
[2]   HIGHLY SELECTIVE, KINETICALLY CONTROLLED ENOLATE FORMATION USING LITHIUM DIALKYLAMIDES IN THE PRESENCE OF TRIMETHYLCHLOROSILANE [J].
COREY, EJ ;
GROSS, AW .
TETRAHEDRON LETTERS, 1984, 25 (05) :495-498
[3]  
COX PJ, 1991, SYNLETT, P321
[4]   ASYMMETRIC-SYNTHESIS USING HOMOCHIRAL LITHIUM AMIDE BASES [J].
COX, PJ ;
SIMPKINS, NS .
TETRAHEDRON-ASYMMETRY, 1991, 2 (01) :1-26
[5]   STRUCTURE AND REACTIVITY OF LITHIUM DIPHENYLAMIDE - ROLE OF AGGREGATES, MIXED AGGREGATES, MONOMERS, AND FREE IONS ON THE RATES AND SELECTIVITIES OF N-ALKYLATION AND E2 ELIMINATION [J].
DEPUE, JS ;
COLLUM, DB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (16) :5524-5533
[6]   ROLE OF HMPT AND TMEDA IN CONTROL OF ENOLATE STEREOCHEMISTRY FOR REACTIONS OF LITHIUM AMIDES WITH 3-PENTANONE [J].
FATAFTAH, ZA ;
KOPKA, IE ;
RATHKE, MW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (11) :3959-3960
[7]   LITHIUM DIISOPROPYLAMIDE MIXED AGGREGATES - STRUCTURES AND CONSEQUENCES ON THE STEREOCHEMISTRY OF KETONE ENOLATE FORMATION [J].
GALIANOROTH, AS ;
KIM, YJ ;
GILCHRIST, JH ;
HARRISON, AT ;
FULLER, DJ ;
COLLUM, DB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (13) :5053-5055
[8]   EFFECTS OF LITHIUM-SALTS ON THE STEREOCHEMISTRY OF KETONE ENOLIZATION BY LITHIUM 2,2,6,6-TETRAMETHYLPIPERIDIDE (LITMP) - A CONVENIENT METHOD FOR HIGHLY E-SELECTIVE ENOLATE FORMATION [J].
HALL, PL ;
GILCHRIST, JH ;
COLLUM, DB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) :9571-9574
[9]   MIXED AGGREGATION OF LITHIUM ENOLATES AND LITHIUM HALIDES WITH LITHIUM 2,2,6,6-TETRAMETHYLPIPERIDIDE (LITMP) [J].
HALL, PL ;
GILCHRIST, JH ;
HARRISON, AT ;
FULLER, DJ ;
COLLUM, DB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) :9575-9585
[10]   THE ROLE OF LITHIUM-SALTS IN CONTROLLING THE REGIOCHEMISTRY OF THE ALKYLATION OF A LITHIUM ENOLATE IN A WEAKLY POLAR APROTIC-SOLVENT [J].
JACKMAN, LM ;
DUNNE, TS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (09) :2805-2806