Nucleophilic addition to silyl-protected five-membered ring oxocarbenium ions governed by stereoelectronic effects

Vi Tuong Tran; K. A. Woerpel

doi:10.1021/jo400945j

Nucleophilic addition to silyl-protected five-membered ring oxocarbenium ions governed by stereoelectronic effects

Vi Tuong Tran, K. A. Woerpel

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

A series of fused-bicyclic acetals containing a disiloxane ring was investigated to evaluate the source of selectivity in silyl-protected 2-deoxyribose systems. The disiloxane ring unexpectedly enables the diaxial conformer of the cation to be stabilized by an electronegative atom at C-3. This low energy conformer subsequently undergoes stereoelectronically controlled nucleophilic addition to give substituted tetrahydrofurans with high diastereoselectivity.

Original language	English (US)
Pages (from-to)	6609-6621
Number of pages	13
Journal	Journal of Organic Chemistry
Volume	78
Issue number	13
DOIs	https://doi.org/10.1021/jo400945j
State	Published - Jul 5 2013

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo400945j

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abstract = "A series of fused-bicyclic acetals containing a disiloxane ring was investigated to evaluate the source of selectivity in silyl-protected 2-deoxyribose systems. The disiloxane ring unexpectedly enables the diaxial conformer of the cation to be stabilized by an electronegative atom at C-3. This low energy conformer subsequently undergoes stereoelectronically controlled nucleophilic addition to give substituted tetrahydrofurans with high diastereoselectivity.",

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Nucleophilic addition to silyl-protected five-membered ring oxocarbenium ions governed by stereoelectronic effects

Abstract

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