title: Tertiary alcohols as substrates for S(N)2-like stereoinversion.
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.
authors.affiliation: Department Chemie, Technische Universität München, Lichtenbergstrasse 4, 85747 Garching (Germany).
authors.forename: Andreas F B
authors.initials: AF
authors.lastname: Räder
authors.forename: Konrad
authors.initials: K
authors.lastname: Tiefenbacher
keywords: isocyanides; nucleophilic substitution; stereoinversion; tertiary alcohols