HIGH DIASTEREOFACIAL SELECTIVITY IN THE REACTION OF SILYL ENOL ETHERS WITH CHLOROSULFIDES

被引:8
作者
IQBAL, J
SHUKLA, A
机构
[1] Dept. of Chemistry, Indian Institute of Technology, Kanpur
关键词
D O I
10.1016/S0040-4020(01)96197-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The chlorosulfides 1 or 2 react with silyl enol ethers in presence of anhydrous zinc bromide to give mainly the corresponding syn products 4 or 6 respectively. The high syn selectivity of these reaction is explained by nucleophilic addition to a Chelated Chiral thionium ion.
引用
收藏
页码:8753 / 8766
页数:14
相关论文
共 39 条
[11]  
Groebel BT, 1977, SYNTHESIS-STUTTGART, P357
[12]   CHEMISTRY OF ORGANOSILICON COMPOUNDS .91. ALLYLSILANES AS SYNTHETIC INTERMEDIATES .2. SYNTHESES OF HOMOALLYL ETHERS FROM ALLYLSILANES AND ACETALS PROMOTED BY TITANIUM TETRACHLORIDE [J].
HOSOMI, A ;
ENDO, M ;
SAKURAI, H .
CHEMISTRY LETTERS, 1976, (09) :941-942
[13]   CHEMISTRY OF CARBANIONS .18. PREPARATION OF TRIMETHYLSILYL ENOL ETHERS [J].
HOUSE, HO ;
CZUBA, LJ ;
GALL, M ;
OLMSTEAD, HD .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (08) :2324-&
[14]   ALLYLATION OF ALDEHYDES WITH ETHERIFICATION BY DIALKOXYDICHLOROTITANIUM ALLYLTRIMETHYLSILANE - AN ASYMMETRIC VARIANT OF THE SAKURAI REACTION [J].
IMWINKELRIED, R ;
SEEBACH, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (09) :765-766
[15]   PHENYLTHIOMETHYLSTANNYLATION OF SILYL ENOL ETHERS AND SILYL DIENOL ETHERS [J].
IQBAL, J ;
MOHAN, R .
TETRAHEDRON LETTERS, 1989, 30 (02) :239-242
[16]  
IQBAL J, 1990, TETRAHEDRON, V46, P6423
[17]   A REGIOSPECIFIC SYNTHESIS OF GAMMA-KETO ESTERS - THE ALKYLATION OF O-SILYLATED ENOLATES WITH METHYL ALPHA-CHLORO-PHENYLTHIOACETATE ALPHA-PHENYLTHIOACETATE [J].
LEE, TV ;
OKONKWO, JO .
TETRAHEDRON LETTERS, 1983, 24 (03) :323-326
[18]   SELECTIVE REACTIONS USING ORGANO-ALUMINUM REAGENTS [J].
MARUOKA, K ;
YAMAMOTO, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (08) :668-682
[19]   ASYMMETRIC REDUCTION OF KETONE REDUCTIVE CLEAVAGE OF CHIRAL ACETALS USING ORGANO-ALUMINUM REAGENTS [J].
MORI, A ;
FUJIWARA, J ;
MARUOKA, K ;
YAMAMOTO, H .
TETRAHEDRON LETTERS, 1983, 24 (42) :4581-4584
[20]   ACYCLIC STEREOSELECTION - HIGH DIASTEREOFACIAL SELECTIVITY IN NUCLEOPHILIC ADDITIONS TO CHIRAL THIONIUM IONS [J].
MORI, I ;
BARTLETT, PA ;
HEATHCOCK, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (23) :7199-7200