{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Nagamalla S"],"funding":["National Institute of General Medical Sciences","NIGMS NIH HHS"],"pagination":["939-943"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC8965746"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["24(3)"],"pubmed_abstract":["We present a new ring-opening reaction of epoxides by pendant silanols, catalyzed by either Ph<sub>3</sub>C<sup>+</sup>BF<sub>4</sub><sup>-</sup> or BINOL-phosphoric acid. Silanol epoxides derived from <i>trans</i>-allylic alcohols, <i>cis</i>-allylic alcohols, <i>trans</i>-homoallylic alcohols, and <i>cis</i>-homoallylic alcohols were all compatible and gave products from either <i>endo</i>- or <i>exo</i>-ring opening. With silanol epoxides derived from 4-alkenyl silanols, an unusual rearrangement to tetrahydrofuran products was observed. The utility of this methodology was demonstrated in a short preparation of protected d-arabitol."],"journal":["Organic letters"],"pubmed_title":["Ring Opening of Epoxides by Pendant Silanols."],"pmcid":["PMC8965746"],"funding_grant_id":["R35 GM142499","R35GM142499"],"pubmed_authors":["Sathyamoorthi S","Nagamalla S","Mague JT"],"additional_accession":[]},"is_claimable":false,"name":"Ring Opening of Epoxides by Pendant Silanols.","description":"We present a new ring-opening reaction of epoxides by pendant silanols, catalyzed by either Ph<sub>3</sub>C<sup>+</sup>BF<sub>4</sub><sup>-</sup> or BINOL-phosphoric acid. Silanol epoxides derived from <i>trans</i>-allylic alcohols, <i>cis</i>-allylic alcohols, <i>trans</i>-homoallylic alcohols, and <i>cis</i>-homoallylic alcohols were all compatible and gave products from either <i>endo</i>- or <i>exo</i>-ring opening. With silanol epoxides derived from 4-alkenyl silanols, an unusual rearrangement to tetrahydrofuran products was observed. The utility of this methodology was demonstrated in a short preparation of protected d-arabitol.","dates":{"release":"2022-01-01T00:00:00Z","publication":"2022 Jan","modification":"2025-04-04T19:10:02.183Z","creation":"2025-04-04T19:10:02.183Z"},"accession":"S-EPMC8965746","cross_references":{"pubmed":["35041437"],"doi":["10.1021/acs.orglett.1c04310"]}}