CHELATION CONTROLLED REACTIONS OF ET2ALCL AND CARBOMETHOXY SUBSTITUTED DIOXOLANES

被引：3
作者：
CASTELLINO, S
VOLK, DE
机构：
[1] Department of Chemistry, North Dakota State University, Fargo
来源：
TETRAHEDRON LETTERS | 1993年 / 34卷 / 06期
关键词：
CHELATION CONTROL; PENTACOORDINATE ALUMINUM; ET2ALCL; DIOXOLANES; NMR;
D O I：
10.1016/S0040-4039(00)77467-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Chelation controlled, regioselective transfer of an alkyl group from one equivalent of Et2AlCl to the ketal carbon of 1 was observed by variable temperature NMR studies. The steric difference between the two R groups in 1 appears to mediate the stereochemical outcome of products 2. The intermediacy of chlorinated products is also reported.
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页码：967 / 970
页数：4
相关论文
共 25 条
[1]   AN EFFICIENT PROCEDURE FOR THE REGIOSELECTIVE MONOPROTECTION OF 1,2-DIOLS [J].
BARTON, DHR ;
ZHU, JP .
TETRAHEDRON, 1992, 48 (39) :8337-8346
[2]   STRUCTURE OF BISTRIMETHYLAMINE-ALUMINIUM TRICHLORIDE, BISTRIMETHYLPHOSPHINE-ALUMINIUM TRICHLORIDE, AND BISTRIMETHYLPHOSPHINE-INDIUM TRICHLORIDE . SINGLE-CRYSTAL RAMAN SPECTRUM OF BISTRIMETHYLAMINE-ALUMINIUM TRICHLORIDE [J].
BEATTIE, IR ;
OZIN, GA ;
BLAYDEN, HE .
JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1969, (17) :2535-&
[3]   CHELATION AND NON-CHELATION DIRECTED CLEAVAGE OF ACETALS [J].
CORCORAN, RC .
TETRAHEDRON LETTERS, 1990, 31 (15) :2101-2104
[4]   CRYSTAL AND MOLECULAR-STRUCTURE OF THE 1-2 ALUMINUM TRICHLORIDE-TETRAHYDROFURAN COMPLEX ALCL3.2THF [J].
COWLEY, AH ;
CUSHNER, MC ;
DAVIS, RE ;
RILEY, PE .
INORGANIC CHEMISTRY, 1981, 20 (04) :1179-1181
[5]   SPECTROSCOPIC INVESTIGATIONS OF COMPLEXES BETWEEN ACETONITRILE AND ALUMINUM TRICHLORIDE .2. STUDY OF ALCL3 IN ACETONITRILE MIXTURES OF TETRAMETHYLAMMONIUM CHLORIDE, WATER, OR NITROMETHANE [J].
DALIBART, M ;
DEROUAULT, J ;
GRANGER, P .
INORGANIC CHEMISTRY, 1982, 21 (06) :2241-2246
[6]   ON THE STEREOSELECTIVE OPENING OF ACHIRAL DIOXANE ACETALS [J].
DENMARK, SE ;
ALMSTEAD, NG .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (22) :6458-6467
[7]   STUDIES ON THE MECHANISM AND ORIGIN OF STEREOSELECTIVE OPENING OF CHIRAL DIOXANE ACETALS [J].
DENMARK, SE ;
ALMSTEAD, NG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (21) :8089-8110
[8]   SPECTROSCOPIC INVESTIGATION OF ALUMINUM TRIHALIDE-TETRAHYDROFURAN COMPLEXES .2. SOLUTIONS OF ALUMINUM-CHLORIDE OR BROMIDE IN TETRAHYDROFURAN AND IN TETRAHYDROFURAN-DICHLOROMETHANE [J].
DEROUAULT, J ;
GRANGER, P ;
FOREL, MT .
INORGANIC CHEMISTRY, 1977, 16 (12) :3214-3218
[9]  
ELIEL EL, 1983, ASYMMETRIC SYNTHESIS, V2, pCH5
[10]  
Evans D. A., 1983, ASYMMETRIC SYNTHESIS, V2
123