Issue 45, 2021

Low catalyst loading enabled organocatalytic synthesis of chiral bis-heterocyclic frameworks containing pyrazole and isoxazole

Abstract

The organocatalytic asymmetric synthesis of enantiopure bis-heterocyclic molecules containing pyrazole and isoxazole under mild reaction conditions has been reported via a low-catalyst loading Michael addition reaction of pyrazolyl nitroalkenes with 1,3-dicarbonyl derivatives. 4-Substituted pyrazole derivatives were obtained in 60–87% yields and with 82–97% ee. These pyrazolyl derivatives are further transformed into chiral bis-heterocyclic derivatives in up to 82% yields and up to 99% ee. The synthesized pyrazole and isoxazole based bis-heterocyclic derivatives are potential bio-active molecules expected to have significant applications. Additionally, the synthesis of these bis-heterocycles can efficiently be carried out in one pot without any loss of enantiopurity, which further adds to its significance.

Graphical abstract: Low catalyst loading enabled organocatalytic synthesis of chiral bis-heterocyclic frameworks containing pyrazole and isoxazole

Supplementary files

Article information

Article type
Paper
Submitted
06 Jul 2021
Accepted
20 Oct 2021
First published
21 Oct 2021

Org. Biomol. Chem., 2021,19, 9910-9924

Low catalyst loading enabled organocatalytic synthesis of chiral bis-heterocyclic frameworks containing pyrazole and isoxazole

B. P. Kaur, V. Sharma, S. C. Sahoo and S. S. Chimni, Org. Biomol. Chem., 2021, 19, 9910 DOI: 10.1039/D1OB01313K

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