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Synthesis 2017; 49(16): 3670-3675
DOI: 10.1055/s-0036-1589040
DOI: 10.1055/s-0036-1589040
paper
Boronic Acid Catalysis for Aza-Piancatelli Rearrangement
Generous financial support from the National Natural Science Foundation of China (21202081), the Natural Science Foundation of Jiangsu Province (BK2012297), Research Fund for the Doctoral Program of Higher Education of China (20120091120026), and Nanjing University is gratefully acknowledged.Further Information
Publication History
Received: 17 April 2017
Accepted after revision: 05 May 2017
Publication Date:
20 June 2017 (online)
‡ These authors contributed equally to this work
Abstract
A first example of boronic acid catalyzed intermolecular aza-Piancatelli rearrangement to access a wide range of trans-4,5-disubstituted cyclopentenones is described. The catalytic system can also be extended to intramolecular aza-Piancatelli rearrangement to afford a wide range of azaspirocycles. Good to excellent yields were obtained in an excellent diastereoselective manner.
Key words
boronic acid - aza-Piancatelli rearrangement - furylcarbinols - cyclopentenones - azaspirocyclesSupporting Information
- Supporting information for this article is available online at https://doi.org /10.1055/s-0036-1589040.
- Supporting Information
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For Nazarov reactions and Pauson–Khand reactions, see:
For recent examples, see:
For reviews of BAC, see: