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Synthesis 2017; 49(16): 3676-3685
DOI: 10.1055/s-0036-1589030
DOI: 10.1055/s-0036-1589030
paper
Highly Regio- and Diastereoselective [3+2]-Annulation Reaction of Morita–Baylis–Hillman Carbonates with Pyrazolones Catalyzed by Tertiary Phosphines
We thank the National Natural Science Foundation of China (21072102), the Committee of Science and Technology of Tianjin (15JCYBJC20700), and State Key Laboratory of Elemento-Organic Chemistry in Nankai University for financial support.Further Information
Publication History
Received: 15 March 2017
Accepted after revision: 17 April 2017
Publication Date:
18 May 2017 (online)
Abstract
A phosphine-catalyzed [3+2] annulation between N-phenylpyrazolone derivatives and Morita–Baylis–Hillman carbonates for the synthesis of chiral heterocyclic systems containing spiro[cyclopentane-3,3′-pyrazole] scaffolds has been developed. The reaction afforded the desired products in moderate to high yields (up to 97%) with good to excellent diastereoselectivities (up to 20:1). A plausible reaction mechanism has also been proposed based on previous literature.
Key words
phosphine catalysis - MBH carbonate - pyrazolones - spiro[cyclopentane-3,3′-pyrazole] - asymmetric synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org /10.1055/s-0036-1589030.
- Supporting Information
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For selected reviews on phosphine-catalyzed annulations, see:
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Selected papers on the annulation of MBH acetates and carbonates in the presence of tertiary phosphine: