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2005•Organic LettersRequires access

Spontaneous Racemization and Epimerization Behavior in Solution of Chiral Nitroxides

Naohiko Ikuma, Hirohito Tsue, Naoko Tsue, Satoshi Shimono, Yoshiaki Uchida, Kazuyoshi Masaki, Nagahisa Matsuoka, Rui Tamura

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Abstract

[reaction: see text] Enantiomerically enriched samples of chiral cyclic nitroxides with a 4-hydroxyphenyl group on the stereogenic center bearing the NO radical group undergo unprecedented spontaneous racemization and/or epimerization in aprotic solvents, which can be well accounted for by the multistep equilibrations involving planar quinoid intermediates.

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[reaction: see text] Enantiomerically enriched samples of chiral cyclic nitroxides with a 4-hydroxyphenyl group on the stereogenic center bearing the NO radical group undergo unprecedented spontaneous racemization and/or epimerization in aprotic solvents, which can be well accounted for by the multistep equilibrations involving planar quinoid intermediates.

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Available abstract

[reaction: see text] Enantiomerically enriched samples of chiral cyclic nitroxides with a 4-hydroxyphenyl group on the stereogenic center bearing the NO radical group undergo unprecedented spontaneous racemization and/or epimerization in aprotic solvents, which can be well accounted for by the multistep equilibrations involving planar quinoid intermediates.

Key concepts: Racemization, Chemistry, Epimer, Stereocenter, Stereochemistry, Medicinal chemistry, Organic chemistry, Enantioselective synthesis

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