title: Kishner's reduction of 2-furylhydrazone gives 2-methylene-2,3-dihydrofuran, a highly reactive ene in the ene reaction.
abstract: [reaction: see text] The Kishner reduction of 2-furylhydrazone gives 2-methylene-2,3-dihydrofuran as the major abnormal reduction product. 2-Methylene-2,3-dihydrofuran is an excellent ene in the carbonyl-ene reaction, reacting with a variety of aldehydes. Most notable was the asymmetric carbonyl-ene reaction of 2-methylene-2,3-dihydrofuran and decanal using Ti(OCH(CH3)2)4/(S)-BINOL to give the corresponding alcohol in 66% yield and 94% ee. The reaction of 2-methylene-2,3-dihydrofuran with 2 equiv of 1,4-benzoquinone unexpectedly gave a monoalkylated 1,4-hydroquinone/1,4-benzoquinone electron donor-acceptor complex.
authors.affiliation: Department of Chemistry, Lafayette College, Easton, Pennsylvania 18042, USA. milesw@lafayette.edu
authors.forename: William H
authors.initials: WH
authors.lastname: Miles
authors.forename: Elizabeth A
authors.initials: EA
authors.lastname: Dethoff
authors.forename: Hannah H
authors.initials: HH
authors.lastname: Tuson
authors.forename: Gözde
authors.initials: G
authors.lastname: Ulas