Issue 47, 2006
From the journal:

Chemical Communications

Synthesis and stereoselective functionalization of silylated heterocycles as a new class of formyl anion equivalents

Alessandro Degl'Innocenti,*a   Salvatore Pollicinob  and  Antonella Capperuccia  

* Corresponding authors

a Dipartimento di Chimica Organica and HBL, via della Lastruccia 13, Italy
E-mail: alessandro.deglinnocenti@unifi.it
Fax: +39 0554573531
Tel: +39 0554573551

b Dipartimento di Chimica Organica “A. Mangini”, viale Risorgimento 4, Italy

Abstract

The fluoride ion-induced reactivity of a series of silyl heterocycles leads to the generation of nucleophilic species capable of interacting with electrophiles, thus disclosing new classes of formyl and acyl anion synthons. Moreover, when reacting stereodefined molecules, the stereoinformation of the reacting carbon–silicon bond is transferred to the newly formed carbon–carbon bond, suggesting possible applications in stereoselective synthesis. Thus, silyl dithiolanes, oxathiolanes, dioxolanes, thiazolidines and oxazolidines can be efficiently and stereoselectively functionalized under fluoride ion conditions in the presence of electrophiles. While direct access to silyl heterocycles is generally either prevented or troublesome, a novel protocol for their synthesis has also been developed, together with a simple general access route to several functionalized and stereodefined mercaptans, building blocks for the construction of silyl heterocycles.

Graphical abstract: Synthesis and stereoselective functionalization of silylated heterocycles as a new class of formyl anion equivalents

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Article information

DOI
https://doi.org/10.1039/B608816N
Article type
Feature Article
Submitted
21 Jun 2006
Accepted
25 Jul 2006
First published
05 Sep 2006

Chem. Commun., 2006, 4881-4893

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Synthesis and stereoselective functionalization of silylated heterocycles as a new class of formyl anion equivalents

A. Degl'Innocenti, S. Pollicino and A. Capperucci, Chem. Commun., 2006, 4881 DOI: 10.1039/B608816N

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