Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 8, Issue -, Pages 1710-1720Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.8.195
Keywords
aza-Michael; domino; hydrazine; organocatalysis; pyrazolidine
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Funding
- National Natural Science Foundation of China [21072145, 21272166]
- Foundation for the Author of National Excellent Doctoral Dissertation of PR China [200931]
- Natural Science Foundation of Jiangsu Province of China [BK2009115]
- Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD)
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The catalytic synthesis of nitrogen-containing heterocycles is of great importance to medicinal and synthetic chemists, and also a challenge for modern chemical methodology. In this paper, we report the synthesis of pyrazolidine derivatives through a domino aza-Michael/hemiacetal sequence with chiral or achiral secondary amines as organocatalysts. Thus, a series of achiral pyrazolidine derivatives were obtained with good yields (up to 90%) and high diastereoselectivities (>20:1) with pyrrolidine as an organocatalyst, and enantioenriched pyrazolidines are also achieved with good results (up to 86% yield, >10/1 regioselectivity, >20:1 dr, 99% ee) in the presence of (S)-diphenylprolinol trimethylsilyl ether catalyst.
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