Intramolecular Hydrogen Bonding in α-Epoxy Alcohols: A Conformational Analysis of 1,2-Dialkyl-2,3-epoxycyclopentanol Diastereomers

Intramolecular Hydrogen Bonding in α-Epoxy Alcohols: A Conformational Analysis of 1,2-Dialkyl-2,3-epoxycyclopentanol Diastereomers

Geometry optimizations for 11 1,2-disubstituted-2,3-epoxycyclopentanol diastereomers were studied using the M06-2X/cc-pVTZ method and basis set to probe mechanistic details in the α-epoxy alcohol semipinacol rearrangement reaction. Electronic energies of active cis diastereomers are on average 0.9 k...

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Veröffentlicht in:Chemistry letters 2018-02, Vol.47 (2), p.156-159
Hauptverfasser: Abdo, Yasmeen A., Weeks, Justin W., Layfield, William, Tremlett, William M., Graham, Joshua W., Tabor, Mikayla E., Causey, Sarah E., Carr, Jeremy M., Tschumper, Gregory S.
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container_end_page 159
container_issue 2
container_start_page 156
container_title Chemistry letters
container_volume 47
creator Abdo, Yasmeen A.
Weeks, Justin W.
Layfield, William
Tremlett, William M.
Graham, Joshua W.
Tabor, Mikayla E.
Causey, Sarah E.
Carr, Jeremy M.
Tschumper, Gregory S.
description Geometry optimizations for 11 1,2-disubstituted-2,3-epoxycyclopentanol diastereomers were studied using the M06-2X/cc-pVTZ method and basis set to probe mechanistic details in the α-epoxy alcohol semipinacol rearrangement reaction. Electronic energies of active cis diastereomers are on average 0.9 kcal mol−1 lower than trans diastereomers. Intramolecular hydrogen bonding stabilizes the cis substrate energy by 3.4 kcal mol−1, on average.
doi_str_mv 10.1246/cl.170932
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title Intramolecular Hydrogen Bonding in α-Epoxy Alcohols: A Conformational Analysis of 1,2-Dialkyl-2,3-epoxycyclopentanol Diastereomers
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