Remote asymmetric induction in organocopper conjugate additions to 3-ketoacrylates.

被引:24
作者
Captain, LF [1 ]
Xia, XY [1 ]
Liotta, DC [1 ]
机构
[1] EMORY UNIV,SANFORD S ATWOOD CHEM CTR,ATLANTA,GA 30322
关键词
D O I
10.1016/0040-4039(96)00828-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Remote asymmetric induction has been achieved in the conjugate addition of organocopper reagents to a novel 3-ketoacrylate system, 1. Conjugate additions proceed in moderate to good yield and with high regio- and scereoselectivity in the presence of diethylaluminum chloride. Copyright (C) 1996 Elsevier Science Ltd.
引用
收藏
页码:4293 / 4296
页数:4
相关论文
共 23 条
[1]   THE SYNTHESIS OF (2S,4S,5S)-5-(N-BOC)-AMINO-6-CYCLOHEXYL-4-HYDROXY-2-ISOPROPYL-HEXANOICACID LACTONE, AN HYDROXYETHYLENE DIPEPTIDE ISOSTERE PRECURSOR [J].
CHAKRAVARTY, PK ;
DELASZLO, SE ;
SARNELLA, CS ;
SPRINGER, JP ;
SCHUDA, PF .
TETRAHEDRON LETTERS, 1989, 30 (04) :415-418
[2]   COORDINATIVELY INDUCED 1,4-DIASTEREOSELECTION IN THE REACTION OF ACYCLIC ALPHA,BETA-ENONES WITH ORGANOCOPPER REAGENTS - A NEW TYPE OF ORGANOCOPPER REAGENT [J].
COREY, EJ ;
HANNON, FJ ;
BOAZ, NW .
TETRAHEDRON, 1989, 45 (02) :545-555
[3]   STEREOCONTROLLED ADDITION OF PROPIONATE HOMOENOLATE EQUIVALENTS TO CHIRAL ALPHA-AMINO ALDEHYDES [J].
DECAMP, AE ;
KAWAGUCHI, AT ;
VOLANTE, RP ;
SHINKAI, I .
TETRAHEDRON LETTERS, 1991, 32 (16) :1867-1870
[4]  
DEZIEL R, UNPUB
[5]   ALDOL REACTIONS OF ALPHA-(N,N-DIBENZYLAMINO) ETHYL KETONES [J].
GOH, JB ;
LAGU, BR ;
WURSTER, J ;
LIOTTA, DC .
TETRAHEDRON LETTERS, 1994, 35 (33) :6029-6032
[6]   REACTIONS INVOLVING ELECTRON-TRANSFER .3. CONJUGATE ADDITION OF LITHIUM DIMETHYLCUPRATE TO ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS [J].
HOUSE, HO ;
UMEN, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (15) :5495-&
[7]   REACTIONS INVOLVING ELECTRON-TRANSFER .12. EFFECTS OF SOLVENT AND SUBSTITUENTS UPON ABILITY OF LITHIUM DIORGANOCUPRATES TO ADD TO ENONES [J].
HOUSE, HO ;
WILKINS, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (12) :2443-2454
[8]  
IBUKA T, 1985, J ORGANOMET CHEM C, V18, P287
[9]   SYNTHESIS OF TRP-VAL NON-CLEAVABLE DIPEPTIDE TRANSITION-STATE ISOSTERES [J].
KORNBERG, BE ;
DOHERTY, AM .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (06) :1257-1262
[10]   HIGHLY DIASTEREOSELECTIVE ALDOL REACTIONS OF CHIRAL METHYL KETONES [J].
LAGU, BR ;
CRANE, HM ;
LIOTTA, DC .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16) :4191-4193