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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
Autor*innen
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.
Weitere Informationen
Publikationsverlauf
Received: 15. März 2017
Accepted after revision: 17. April 2017
Publikationsdatum:
18. Mai 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 (PDF) (opens in new window)
-
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