Direct Synthesis of Polysubstituted Aluminoisoxazoles and Pyrazoles by a Metalative Cyclization

Alumino-heteroles are obtained from simple precursors in a fully chemo- and regioselective manner by a metalative cyclization. The carbon–aluminum bond is still able to react further with several electrophiles, without the need of transmetalation. This synthetic route provides a novel entry to heter...

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Bibliographic Details
Published in:Organic letters 2011-10, Vol.13 (20), p.5664-5667
Main Authors: Jackowski, Olivier, Lecourt, Thomas, Micouin, Laurent
Format: Article
Language:English
Subjects:
Aluminum - chemistry
Catalysis
Chemical Sciences
Cyclization
Isoxazoles - chemical synthesis
Isoxazoles - chemistry
Molecular Structure
Organic chemistry
Organometallic Compounds - chemical synthesis
Organometallic Compounds - chemistry
Pyrazoles - chemical synthesis
Pyrazoles - chemistry
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Summary:Alumino-heteroles are obtained from simple precursors in a fully chemo- and regioselective manner by a metalative cyclization. The carbon–aluminum bond is still able to react further with several electrophiles, without the need of transmetalation. This synthetic route provides a novel entry to heterocyclic organoaluminum reagents as well as a straightforward access to 3,4,5-trisubstituted isoxazoles and 1,3,4,5-tetrasubstituted pyrazoles.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol202389u