Kishner's reduction of 2-furylhydrazone gives 2-methylene-2,3-dihydrofuran, a highly reactive ene in the ene reaction.
[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.
Miles
William H
WH
Department of Chemistry, Lafayette College, Easton, Pennsylvania 18042, USA. milesw@lafayette.edu
Dethoff
Elizabeth A
EA
Tuson
Hannah H
HH
Ulas
Gözde
G