SN2'-REGIOSELECTIVE AND DIASTEREOSELECTIVE ALLYLATION OF ORGANOZINC REAGENTS

被引:13
作者
ARAI, M [1 ]
KAWASUJI, T [1 ]
NAKAMURA, E [1 ]
机构
[1] TOKYO INST TECHNOL, DEPT CHEM, MEGURO KU, TOKYO 152, JAPAN
关键词
D O I
10.1246/cl.1993.357
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Dialkylzinc reagents, R2Zn and R2Zn.LiCl, undergo an S(N)2'-regio- and diastereoselective allylation reaction with substituted allylic chlorides and phosphates in the presence of a coordinating additive.
引用
收藏
页码:357 / 360
页数:4
相关论文
共 18 条
[1]   MECHANISTIC ASPECTS ON THE FORMATION OF CHIRAL ALLENES FROM PROPARGYLIC ETHERS AND ORGANOCOPPER REAGENTS [J].
ALEXAKIS, A ;
MAREK, I ;
MANGENEY, P ;
NORMANT, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :8042-8047
[2]   COPPER-CATALYZED REACTIONS OF ORGANOTITANIUM REAGENTS - HIGHLY SN2' SELECTIVE AND ANTI-SELECTIVE AND DIASTEREOSELECTIVE AND CHEMOSELECTIVE ALKYLATION OF ALLYLIC CHLORIDES AND PHOSPHATES [J].
ARAI, M ;
NAKAMURA, E ;
LIPSHUTZ, BH .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (19) :5489-5493
[3]   TRANSITION-METAL-CATALYZED GRIGNARD REACTION OF SECONDARY ALLYLIC PHOSPHATES [J].
ARAKI, S ;
BUTSUGAN, Y .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (05) :969-972
[4]   SYNTHESES OF ISOCARBACYCLIN BY HIGHLY REGIOSELECTIVE ALKYLATION OF ALLYLIC ALCOHOLS [J].
BANNAI, K ;
TANAKA, T ;
OKAMURA, N ;
HAZATO, A ;
SUGIURA, S ;
MANABE, K ;
TOMIMORI, K ;
KATO, Y ;
KUROZUMI, S ;
NOYORI, R .
TETRAHEDRON, 1990, 46 (19) :6689-6704
[5]   STEREOSELECTIVE ADDITION OF ORGANOCUPRATES TO A CHIRAL ALPHA-BETA ETHYLENIC OXAZOLIDINE - MECHANISM, NATURE AND REACTIVITY OF THE INTERMEDIATES [J].
BERLAN, J ;
BESACE, Y ;
POURCELOT, G ;
CRESSON, P .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1983, 256 (01) :181-192
[6]  
BOURGAINCOMMERC.M, 1977, J CHEM RES SYNOP, P183
[7]   AUXILIARY-BASED, ASYMMETRIC SN2' REACTIONS - A CASE OF 1,7-RELATIVE STEREOGENESIS [J].
DENMARK, SE ;
MARBLE, LK .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (07) :1984-1986
[8]   SYNTHETIC USE OF AN UNUSUAL ORGANOCUPRATE INTERMEDIATE [J].
DOLLAT, JM ;
LUCHE, JL ;
CRABBE, P .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (21) :761-762
[9]   DIASTEREOSELECTIVE ADDITION ON A C=C DOUBLE-BOND IN THE ALPHA POSITION OF A CHIRAL OXAZOLIDINE [J].
HUCHE, M ;
AUBOUET, J ;
POURCELOT, G ;
BERLAN, J .
TETRAHEDRON LETTERS, 1983, 24 (06) :585-586
[10]   HIGHLY SELECTIVE SYNTHESIS OF (E)-ALKENE ISOSTERIC DIPEPTIDES WITH HIGH OPTICAL PURITY VIA RCU(CN)LI.BF3 MEDIATED REACTION [J].
IBUKA, T ;
HABASHITA, H ;
FUNAKOSHI, S ;
FUJII, N ;
OGUCHI, Y ;
UYEHARA, T ;
YAMAMOTO, Y .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (07) :801-803