Stereoretentive Halogenations and Azidations with Titanium(IV) Enabled by Chelating Leaving Groups

Titanium does it again! With the help of nucleophile‐assisting leaving groups (NALGs), alkyl bromides, iodides, and, for the first time, azides are obtained from sulfonates with complete retention of configuration. Critical to the design of these new titanium(IV) reactions has been the use of NALGs...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2008-09, Vol.47 (39), p.7511-7514
Main Authors: Lepore, Salvatore D, Mondal, Deboprosad, Li, Song Ye, Bhunia, Anjan K
Format: Article
Language:English
Subjects:
azides
Azides - chemistry
Chelating Agents - chemical synthesis
Chelating Agents - chemistry
Halogenation
leaving groups
Molecular Structure
nucleophilic substitution
Stereoisomerism
Temperature
titanium
Titanium - chemistry
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Summary:Titanium does it again! With the help of nucleophile‐assisting leaving groups (NALGs), alkyl bromides, iodides, and, for the first time, azides are obtained from sulfonates with complete retention of configuration. Critical to the design of these new titanium(IV) reactions has been the use of NALGs which are thought to chelate the Lewis acid reagent in the transition state promoting an SNi‐type mechanism.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200802472