jo800967p_si_002.cif (38.3 kB)
5- and 6-Exocyclic Products, cis-2,3,5-Trisubstituted Tetrahydrofurans, and cis-2,3,6-Trisubstituted Tetrahydropyrans via Prins-Type Cyclization
dataset
posted on 2008-10-03, 00:00 authored by Satish.
N. Chavre, Hyunah Choo, Jae Kyun Lee, Ae Nim Pae, Youseung Kim, Yong Seo ChoExocyclic products having cis-2,5 and cis-2,6 substitution were synthesized from terminally substituted
alkynyl alcohols with various aldehydes via Prins-type cyclization
in good yields. It is of interest that synthesized 5- and 6-exocyclic
vinyl cations generated as a result of Prins-type cyclization could
be trapped as a vinyl triflate in CH2Cl2 to
give 3-furanylidenes and 3-pyranylidenes. Those 3-furanylidenes and
3-pyranylidenes underwent hydrolysis to give the corresponding 3-acyl-substituted
products having all-cis-configured
isomers, such as 2,3,5-trisubstituted tetrahydrofurans and 2,3,6-trisubstituted
tetrahydropyrans.