alexa Organocatalytic cascade aza-Michael hemiacetal reaction between disubstituted hydrazines and α,β-unsaturated aldehydes: Highly diastereo- and enantioselective synthesis of pyrazolidine derivatives.
Pharmaceutical Sciences

Pharmaceutical Sciences

Journal of Bioequivalence & Bioavailability

Author(s): Geng ZC, Chen J, Li N, Huang XF, Zhang Y,

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Abstract 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.
This article was published in Beilstein J Org Chem and referenced in Journal of Bioequivalence & Bioavailability

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