5-Exocyclic products, 2,3,5-trisubstituted tetrahydrofurans via Prins-type cyclization.
[reaction: see text] 5-Exocyclic products, 2,3,5-trisubstituted tetrahydrofurans, were synthesized from homopropargylic alcohols with terminally substituted alkynes and various aldehydes via Prins-type cyclization. It is of interest that the exocyclic vinyl cation generated as a result of Prins-type cyclization could be trapped as a vinyl triflate when CH2Cl2 was used as a solvent, whereas in ethereal solution the vinyl cation underwent hydrolysis to give the corresponding ketone product.
Chavre
Satish N
SN
Biochemicals Research Center, Korea Institute of Science and Technology, P.O. Box 131, Cheongryang, Seoul 130-650, Korea.
Choo
Hyunah
H
Cha
Joo Hwan
JH
Pae
Ae Nim
AN
Choi
Kyung Il
KI
Cho
Yong Seo
YS