Tertiary alcohols as substrates for S(N)2-like stereoinversion

Andreas F B Räder; Konrad Tiefenbacher

doi:10.1002/anie.201308803

Tertiary alcohols as substrates for S(N)2-like stereoinversion

Angew Chem Int Ed Engl. 2014 Jan 27;53(5):1206-7. doi: 10.1002/anie.201308803. Epub 2013 Dec 4.

Authors

Andreas F B Räder¹, Konrad Tiefenbacher

Affiliation

¹ Department Chemie, Technische Universität München, Lichtenbergstrasse 4, 85747 Garching (Germany).

PMID: 24307081
DOI: 10.1002/anie.201308803

Abstract

Rewrite the textbooks! The stereospecific bimolecular substitution reaction (SN 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.

Keywords: isocyanides; nucleophilic substitution; stereoinversion; tertiary alcohols.