Evaluation of Ethyl 2‐Carbomethoxyethenesulfinates as 2‐Hydroxymethyl Enethiol Equivalents in the Diels—Alder Reaction.

Abstract

Cycloaddition reactions O 0070Evaluation of Ethyl 2-Carbomethoxyethenesulfinates as 2-Hydroxymethyl Enethiol Equivalents in the Diels-Alder Reaction. -Both dienophiles (I) and (V) act as masked 2-hydroxymethyl enethiol equivalents in Diels-Alder cycloaddition reactions with various dienes followed by reduction of the resulting cycloadducts. The latter are obtained as mixtures of sulfur epimers which are unified in the subsequent reduction step. Under the appropriate reaction conditions, simultaneous reduction of both the sulfinate and the carboxylate ester functionalities occurs (to be continued). -(FARAGHER, R. J.; ALBERICO, D.; SCHWAN*, A. L.; Tetrahedron 61 (2005) 5, 1115-pp; Guelph-Waterloo Cent. Grad. Work Chem., Dep. Chem. Biochem., Univ. Guelph, Guelph, Ont. N1G 2W1, Can.; Eng.) -Klein 23-039