%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