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Ring Opening of Epoxides by Pendant Silanols.

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.

SUBMITTER: Nagamalla S 

PROVIDER: S-EPMC8965746 | biostudies-literature | 2022 Jan

REPOSITORIES: biostudies-literature

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Ring Opening of Epoxides by Pendant Silanols.

Nagamalla Someshwar S   Mague Joel T JT   Sathyamoorthi Shyam S  

Organic letters 20220118 3

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 rearrangem  ...[more]

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