Stereoselectivity in the thermal cycloaddition reactions of tetrafluoroethylene to derivatives of α-(4-ethoxyphenyl)acrylic acid

Esters of chiral auxiliaries with α-(4-ethoxyphenyl)acrylic acid undergo diastereoselective addition reactions with tetrafluoroethylene at 130°–170° to afford tetrafluorocyclobutanecarboxylic esters. The oxazoline derived from (+)-(1 S,2 R)-norephedrine and α-(4-ethoxyphenyl)acrylic acid shows negli...

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Bibliographic Details
Published in:Tetrahedron letters 1997-06, Vol.38 (24), p.4277-4280
Main Authors: Serelis, Algirdas K., Simpson, Gregory W.
Format: Article
Language:English
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Summary:Esters of chiral auxiliaries with α-(4-ethoxyphenyl)acrylic acid undergo diastereoselective addition reactions with tetrafluoroethylene at 130°–170° to afford tetrafluorocyclobutanecarboxylic esters. The oxazoline derived from (+)-(1 S,2 R)-norephedrine and α-(4-ethoxyphenyl)acrylic acid shows negligible stereoselectivity. Esters of chiral auxiliaries with α-(4-ethoxyphenyl)acrylic acid undergo diastereoselective addition reactions with tetrafluoroethylene at 170° to afford tetrafluorobutane esters.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(97)00878-2