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Ring Opening of Epoxides by Pendant Silanols
Nagamalla, Someshwar Mague, Joel T. Sathyamoorthi, Shyam
Nagamalla, Someshwar
Mague, Joel T.
Sathyamoorthi, Shyam
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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.
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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
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2022-01-18
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American Chemical Society
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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