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Synthesis 2017; 49(16): 3676-3685
DOI: 10.1055/s-0036-1589030
paper
© Georg Thieme Verlag Stuttgart · New York

Highly Regio- and Diastereoselective [3+2]-Annulation Reaction of Morita–Baylis–Hillman Carbonates with Pyrazolones Catalyzed by Tertiary Phosphines

Weiping Zheng
a   State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China   Email: miaozhiwei@nankai.edu.cn
b   Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China
,
Yuming Li
a   State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China   Email: miaozhiwei@nankai.edu.cn
,
Jiayong Zhang
a   State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China   Email: miaozhiwei@nankai.edu.cn
,
Siyi Du
a   State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China   Email: miaozhiwei@nankai.edu.cn
,
Zhiwei Miao  *
a   State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China   Email: miaozhiwei@nankai.edu.cn
b   Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China
c   Collaborative Innovation Center of Chemical Science and Engineering (Tianjin, Tianjin 300071, P. R. of China
› Author AffiliationsWe 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.
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Publication History

Received: 15 March 2017

Accepted after revision: 17 April 2017

Publication Date:
18 May 2017 (online)

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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 synthesis

Supporting Information

    Supporting information for this article is available online at https://doi.org /10.1055/s-0036-1589030.
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