EFFICIENT MERCURY-FREE PREPARATION OF VINYL AND ISOPROPENYL ETHERS OF CHIRAL SECONDARY ALCOHOLS AND ALPHA-HYDROXYESTERS

被引:38
作者
DUJARDIN, G
ROSSIGNOL, S
BROWN, E
机构
[1] Laboratoire de Synthèse Organique (associé au CNRS), Faculté des Sciences, F-72017 Le Mans, Avenue Olivier Messiaen
关键词
D O I
10.1016/0040-4039(95)00087-S
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Mixed acetals 2a-h and 5a-d readily deriving from the alpha-chiral alcohols 1a-h and ethyl vinyl ether or isopropenyl methyl ether, underwent selective elimination of primary alcohol upon treatment with triethylamine and trimethylsilyl trifluoromethanesulfonate, and thus afforded good to high yields of the chiral enol ether 3a-h and 6a-d respectively.
引用
收藏
页码:1653 / 1656
页数:4
相关论文
共 25 条
[1]  
Posner, Wettlaufer, Asymmetric Diels-Alder cycloadditions using chiral alkyl vinyl ethers and a dienyl sulfone, Tetrahedron Letters, 27, pp. 667-670, (1986)
[2]  
Backvall, Rise, Tetrahedron Lett., 30, pp. 5347-5348, (1989)
[3]  
Arnold, Reissig, Hetero Diels-Alder Reactions of Optically Active Enol Ethers with a Nitrosoalkene: Asymmetric Synthesis of 1, 2-Oxazine Derivatives, Synlett, pp. 514-516, (1990)
[4]  
Dujardin, Molato, Brown, Tetrahedron: Asymmetry, 4, pp. 193-196, (1993)
[5]  
Dujardin, Rossignol, Molato, Brown, Tetrahedron, 50, pp. 9037-9050, (1994)
[6]  
Denmark, Senanayake, Ginny, Tetrahedron, 46, pp. 4857-4876, (1990)
[7]  
Choudhury, Franck, Gupta, Tetrahedron Lett., 30, pp. 4921-4924, (1989)
[8]  
Greene, Charbonnier, Tetrahedron Lett., 26, pp. 5525-5528, (1985)
[9]  
Greene, Charbonnier, Luche, Moyano, J. Amer. Chem. Soc., 109, (1987)
[10]  
Watanabe, Conlon, J. Amer. Chem. Soc., 79, pp. 2828-2833, (1957)