ATTENTION: The software behind KU ScholarWorks is being upgraded to a new version. Starting July 15th, users will not be able to log in to the system, add items, nor make any changes until the new version is in place at the end of July. Searching for articles and opening files will continue to work while the system is being updated.
If you have any questions, please contact Marianne Reed at mreed@ku.edu .
Ring Opening of Epoxides by Pendant Silanols
| 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 |
