Ring Opening of Epoxides by Pendant Silanols

Nagamalla, Someshwar; Mague, Joel T.; Sathyamoorthi, Shyam

dc.contributor.author	Nagamalla, Someshwar
dc.contributor.author	Mague, Joel T.
dc.contributor.author	Sathyamoorthi, Shyam
dc.date.accessioned	2022-05-04T15:37:43Z
dc.date.available	2022-05-04T15:37:43Z
dc.date.issued	2022-01-18
dc.identifier.citation	Nagamalla, 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.1c04310	en_US
dc.identifier.uri	http://hdl.handle.net/1808/32754
dc.description	This 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.1c04310	en_US
dc.description.abstract	We 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.	en_US
dc.publisher	American Chemical Society	en_US
dc.rights	Copyright © 2022 American Chemical Society.	en_US
dc.title	Ring Opening of Epoxides by Pendant Silanols	en_US
dc.type	Article	en_US
kusw.kuauthor	Nagamalla, Someshwar
kusw.kuauthor	Sathyamoorthi, Shyam
kusw.kudepartment	Medicinal Chemistry	en_US
dc.identifier.doi	10.1021/acs.orglett.1c04310	en_US
kusw.oaversion	Scholarly/refereed, author accepted manuscript	en_US
kusw.oapolicy	This item meets KU Open Access policy criteria.	en_US
dc.identifier.pmid	PMC8965746	en_US
dc.rights.accessrights	openAccess	en_US

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