Enantioselective [4+ 2]??Cycloaddition Reaction of a Photochemically Generated o??Quinodimethane: Mechanistic Details, Association Studies, and Pressure Effects

…, CN Orlebar, E Herdtweck, M Kaneda…

Index: Grosch, Benjamin; Orlebar, Caroline N.; Herdtweck, Eberhardt; Kaneda, Masayuki; Wada, Takehiko; Inoue, Yoshihisa; Bach, Thorsten Chemistry - A European Journal, 2004 , vol. 10, # 9 p. 2179 - 2189

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Citation Number: 59

Abstract

Abstract 1, 2, 3, 4-Tetrahydro-2-oxoquinoline-5-aldehyde (2) was prepared from m- aminobenzoic acid and 3-ethoxyacryloyl chloride (4) in 19% overall yield. Compound 2 underwent a photochemically induced [4+ 2]-cycloaddition reaction with various dienophiles upon irradiation in toluene solution. The exo product 10 a was obtained with acrylonitrile (9 a) as the dienophile, whereas methyl acrylate (9 b) and dimethyl fumarate (9 c) furnished ...