%0 Generic
%A Chavre, Satish.
N.
%A Choo, Hyunah
%A Lee, Jae Kyun
%A Pae, Ae Nim
%A Kim, Youseung
%A Cho, Yong Seo
%D 2008
%T 5- and 6-Exocyclic Products, cis-2,3,5-Trisubstituted
Tetrahydrofurans, and cis-2,3,6-Trisubstituted Tetrahydropyrans
via Prins-Type Cyclization
%U https://acs.figshare.com/articles/dataset/5_and_6_Exocyclic_Products_i_cis_i_2_3_5_Trisubstituted_Tetrahydrofurans_and_i_cis_i_2_3_6_Trisubstituted_Tetrahydropyrans_via_Prins_Type_Cyclization/2909692
%R 10.1021/jo800967p.s002
%2 https://acs.figshare.com/ndownloader/files/4607911
%K ci
%K Exocyclic
%K CH 2Cl
%K furanylidene
%K cyclization
%K trisubstituted
%K vinyl triflate
%K pyranylidene
%K alkynyl alcohols
%X Exocyclic 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.
%I ACS Publications