Nagamalla, SomeshwarMague, Joel T.Sathyamoorthi, Shyam2022-05-042022-05-042022-01-18Nagamalla, S., Mague, J. T., & Sathyamoorthi, S. (2022). Ring Opening of Epoxides by Pendant Silanols. Organic letters, 24(3), 939–943. https://doi.org/10.1021/acs.orglett.1c04310https://hdl.handle.net/1808/32754This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © 2022 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see doi.org/10.1021/acs.orglett.1c04310We present a new ring-opening reaction of epoxides by pendant silanols, catalyzed by either Ph3C+BF4– or BINOL-phosphoric acid. Silanol epoxides derived from trans-allylic alcohols, cis-allylic alcohols, trans-homoallylic alcohols, and cis-homoallylic alcohols were all compatible and gave products from either endo- or exo-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.Copyright © 2022 American Chemical Society.Article10.1021/acs.orglett.1c04310PMC8965746openAccess