Dimethylaluminum chloride catalyzed ene reactions of aldehydes. 2. Stereochemistry and scope

CP Cartaya-Marin, AC Jackson…

Index: Cartaya-Marin, Claudia P.; Jackson, Andrew C.; Snider, Barry B. Journal of Organic Chemistry, 1984 , vol. 49, # 13 p. 2443 - 2446

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Citation Number: 23

Abstract

The dimethylaluminum chloride (MezAICl) catalyzed ene reactions of aliphatic aldehydes with (E)-and (ZJ-3-methy1-2-pentene (1 and 2) were examined. Complex mix- of erythro and threo adducts and double-bond position isomers were obtained. Ene reaction of 2- phenylpropionaldehyde with methylenecyclohexane gives a 1.5: l mixture of diastereomers. Geraniol, linalool, citral, geranylacetone, and 6-methyl-5-hepten-2-one are suitable ...