Chavre, Satish N. Choo, Hyunah Lee, Jae Kyun Pae, Ae Nim Kim, Youseung Cho, Yong Seo 2024-01-20T22:32:56Z 2024-01-20T22:32:56Z 2021-08-31 2008-10-03 0022-3263 https://pubs.kist.re.kr/handle/201004/133062 Exocyclic proc [GRAPHICS] 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. English AMER CHEMICAL SOC STEREOSELECTIVE-SYNTHESIS 2,3,5-TRISUBSTITUTED TETRAHYDROFURANS STEREOCONTROLLED PREPARATION SYNTHETIC ROUTES ACID EPIMERIZATION DIHYDROPYRANS CONSTRUCTION SUPPRESSION ALDEHYDES 5- and 6-exocyclic products, cis-2,3,5-trisubstituted tetrahydrofurans, and cis-2,3,6-trisubstituted tetrahydropyrans via Prins-type cyclization Article 10.1021/jo800967p 1 JOURNAL OF ORGANIC CHEMISTRY, v.73, no.19, pp.7467 - 7471 JOURNAL OF ORGANIC CHEMISTRY 73 19 7467 7471 scie scopus 000259574700005 2-s2.0-53049102989 Chemistry, Organic Chemistry Article STEREOSELECTIVE-SYNTHESIS 2,3,5-TRISUBSTITUTED TETRAHYDROFURANS STEREOCONTROLLED PREPARATION SYNTHETIC ROUTES ACID EPIMERIZATION DIHYDROPYRANS CONSTRUCTION SUPPRESSION ALDEHYDES Tetrahydrofurans Tetrahydropyrans Prins-Type Cyclization