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Diastereoselective bromine/lithium exchange reactions of 3-alkoxy-1,1-dibromo-alkanes

被引：14
作者：
Hoffmann, RW
Stiasny, HC
Kruger, J
机构：
[1] Philipps-Universität Marburg, Fachbereich Chemie
来源：
TETRAHEDRON | 1996年 / 52卷 / 21期
关键词：
bromine/lithium exchange; 1,3-asymmetric induction; diastereotopic group-differentiation;
D O I：
10.1016/0040-4020(96)00260-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The diastereoselectivity in the bromine/lithium exchange reaction on chiral 3-alkoxy-1,1-dibromo-alkanes has been investigated. The differentiation of the two diastereotopic bromine atoms was found not to depend solely on a conformational preorganization of the substrate, as surmised previously. Ir became apparent that steric crowding at the delta-center controls the spatial orientation of a C-3-oxygen substituent at the chiral center, which may be the cause of the asymmetric induction observed. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码：7421 / 7434
页数：14
相关论文
共 25 条
[1]   THE CONFORMATIONAL EFFECTS OF QUATERNARY CENTERS [J].
ALDER, RW ;
MAUNDER, CM ;
ORPEN, AG .
TETRAHEDRON LETTERS, 1990, 31 (46) :6717-6720
[2]  
BROWN HC, 1979, SYNTHESIS-STUTTGART, P701
[3]   FACTORS AFFECTING EASE OF RING FORMATION - THE EFFECT OF ANCHORING SUBSTITUTION ON THE RATE OF AN INTRAMOLECULAR DIELS-ALDER REACTION WITH FURAN-DIENE [J].
CAUWBERGHS, S ;
DECLERCQ, PJ .
TETRAHEDRON LETTERS, 1988, 29 (20) :2493-2496
[4]   A NEW GENERAL SYNTHETIC ROUTE TO BRIDGED CARBOXYLIC ORTHO ESTERS [J].
COREY, EJ ;
RAJU, N .
TETRAHEDRON LETTERS, 1983, 24 (50) :5571-5574
[5]  
Hoffmann R. W., 1988, ANGEW CHEM, V100, P1232
[6]  
Hoffmann R. W., 1992, ANGEW CHEM, V104, P1147, DOI DOI 10.1002/ANGE.19921040905
[7]  
HOFFMANN RW, 1991, LIEBIGS ANN CHEM, P811
[8]   CHIRAL ORGANOMETALLIC REAGENTS .9. ON THE ORIGINS OF THE DIASTEREOSELECTIVITY IN THE BROMINE LITHIUM EXCHANGE OF 3-ALKOXY-1,1-DIBROMOALKANES [J].
HOFFMANN, RW ;
BRUMM, K ;
BEWERSDORF, M ;
MIKOLAISKI, W ;
KUSCHE, A .
CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (12) :2741-2747
[9]  
HOFFMANN RW, 1992, LIEBIGS ANN CHEM, P1137
[10]   CHIRAL ORGANOMETALLIC REAGENTS .1. STEREOSELECTIVE EXCHANGE OF DIASTEREOTOPIC BROMINE ATOMS BY LITHIUM IN 1,1-DIBROMO-3-(TRIMETHYLSILYLOXY)ALKANES [J].
HOFFMANN, RW ;
BEWERSDORF, M ;
KRUGER, M ;
MIKOLAISKI, W ;
STURMER, R .
CHEMISCHE BERICHTE, 1991, 124 (05) :1243-1252
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