Tertiary Alcohols as Substrates for S sub(N)2-Like Stereoinversion

Rewrite the textbooks! The stereospecific bimolecular substitution reaction (S sub(N)2) is usually limited to primary and secondary electrophiles. The Shenvi group has developed a method in which tertiary alcohol substrates are converted into isocyanides with configurational inversion. Intriguingly,...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 53; no. 5; pp. 1206 - 1207
Main Authors Raeder, Andreas FB, Tiefenbacher, Konrad
Format Journal Article
LanguageEnglish
Published 01.01.2014
Subjects
Alcohols
Inversions
Substitution reactions
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Summary:Rewrite the textbooks! The stereospecific bimolecular substitution reaction (S sub(N)2) is usually limited to primary and secondary electrophiles. The Shenvi group has developed a method in which tertiary alcohol substrates are converted into isocyanides with configurational inversion. Intriguingly, tertiary hydroxy groups react selectively in the presence of unprotected primary and secondary hydroxy groups.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201308803