biostudies-literatureHan XNCRR NIH HHSNIGMS NIH HHS3808-11https://www.ebi.ac.uk/biostudies/studies/S-EPMC3498537biostudies-literatureUnknown14(14)The classical geometry of the 6-endo transition state for nucleophilic additions into oxocarbenium ions can be perturbed by incorporating the reactive groups into medium-sized rings, leading to the formation of 2,6-trans-dialkyl tetrahydropyrans. The bicyclic products exhibit inside-outside stereoisomerism, as seen in numerous macrolide natural products.Organic lettersSynthesis of bridged inside-outside bicyclic ethers through oxidative transannular cyclization reactions.PMC3498537R01 GM062924GM0629241S10RR031789-01Floreancig PEHan XfalseSynthesis of bridged inside-outside bicyclic ethers through oxidative transannular cyclization reactions.The classical geometry of the 6-endo transition state for nucleophilic additions into oxocarbenium ions can be perturbed by incorporating the reactive groups into medium-sized rings, leading to the formation of 2,6-trans-dialkyl tetrahydropyrans. The bicyclic products exhibit inside-outside stereoisomerism, as seen in numerous macrolide natural products.2012-01-01T00:00:00Z2012 Jul2025-04-04T01:06:21.946Z2019-03-27T01:00:33ZS-EPMC34985372278395010.1021/ol301720u