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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
Autoren
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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