Use of α-chlorosulfides in indium promoted C-C couplings:: easy entry into the stereoselective formation of epoxy alkynes

被引:20
作者
Engstrom, G [1 ]
Morelli, M [1 ]
Palomo, C [1 ]
Mitzel, T [1 ]
机构
[1] Trinity Coll, Dept Chem, Hartford, CT 06106 USA
关键词
indium couplings; epoxy alkynes; stereocontrol;
D O I
10.1016/S0040-4039(99)01152-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The use of alpha-chlorosulfide compounds to control stereoselectivity in indium promoted C-C couplings occurs smoothly at room temperature under aqueous and mixed aqueous/organic conditions. Use of the halide to control syn/anti ratios simplifies the indium promoted coupling with respect to earlier studies and is used to gain entry into stereocontrolled epoxy alkynes in good yields. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5967 / 5970
页数:4
相关论文
共 17 条
[1]  
Bohlmann F, 1973, NATURALLY OCCURRING
[2]   1993 RU-LEMIEUX-AWARD-LECTURE - ORGANOMETALLIC-TYPE REACTIONS IN AQUEOUS-MEDIA - A NEW CHALLENGE IN ORGANIC-SYNTHESIS [J].
CHAN, TH ;
LI, CJ ;
LEE, MC ;
WEI, ZY .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (05) :1181-1192
[3]  
ISAAC MB, 1995, TETRAHEDRON LETT, V36, P8957
[4]   Synthesis of chiral epoxyalkynes [J].
Kanger, T ;
Niidas, P ;
Muurisepp, AM ;
Pehk, T ;
Lopp, M .
TETRAHEDRON-ASYMMETRY, 1998, 9 (14) :2499-2508
[5]   TIN-MEDIATED AND INDIUM-MEDIATED ALLYLATION IN AQUEOUS-MEDIA - APPLICATION TO UNPROTECTED CARBOHYDRATES [J].
KIM, E ;
GORDON, DM ;
SCHMID, W ;
WHITESIDES, GM .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) :5500-5507
[6]  
Li C.-J., 1997, ORGANIC REACTIONS AQ
[7]   ORGANIC-REACTIONS IN AQUEOUS-MEDIA - WITH A FOCUS ON CARBON-CARBON BOND FORMATION [J].
LI, CJ .
CHEMICAL REVIEWS, 1993, 93 (06) :2023-2035
[8]   REACTION OF (ALPHA-THIOALKYL)CHROMIUM COMPOUNDS PREPARED BY CHROMIUM(II) REDUCTION OF ALPHA-HALO SULFIDES [J].
NAKATSUKASA, S ;
TAKAI, K ;
UTIMOTO, K .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (25) :5045-5046
[9]  
NORMANT H, 1964, CR HEBD ACAD SCI, V259, P830