Tetrahedron letters

Efficient mercury-free preparation of vinyl and isopropenyl ethers of chiral secondary alcohols and α-hydroxyesters

G Dujardin, S Rossignol, E Brown

Index: Dujardin, Gilles; Rossignol, Sandrine; Brown, Eric Tetrahedron Letters, 1995 , vol. 36, # 10 p. 1653 - 1656

Full Text: HTML

Citation Number: 37

Abstract

Mixed acetals 2a-h and 5a-d, readily deriving from the α-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 ethers 3a-h and 6a-d, respectively.

Related Articles:

Vinyl polymerization versus [1, 3] O to C rearrangement in the ruthenium-catalyzed reactions of vinyl ethers with hydrosilanes

[Harada, Nari-Aki; Nishikata, Takashi; Nagashima, Hideo Tetrahedron, 2012 , vol. 68, # 15 p. 3243 - 3252]

4-Alkoxycarbonyl-and Aminocarbonyl-Substituted Isoxazoles as Masked Acrylates and Acrylamides in the Asymmetric Synthesis of Δ2-Isoxazolines

[Boa, Andrew N.; Dawkins, David A.; Hergueta, Antonio R.; Jenkins, Paul R. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1994 , # 8 p. 953 - 960]

More Articles...