Enantioselective Direct Synthesis of C3-Hydroxyalkylated Pyrrole via an Amine-Catalyzed Aldol/Paal-Knorr Reaction Sequence
Amol Prakash Pawar, Jyothi Yadav, Atul Jankiram Dolas, Yadav Kacharu Nagare, Eldhose Iype, Krishnan Rangan and Indresh Kumar*
*Department of Chemistry, Birla Institute of Technology and Science, Pilani 333031, Rajasthan, India,
Email: indresh.kumar
pilani.bits-pilani.ac.in
A. P. Pawar, J. Yadav, A. J. Dolas, Y. K. Nagare, E. Iype, K. Rangan, I. Kumar, Org. Lett., 2022, 24, 7549-7554.
DOI: 10.1021/acs.orglett.2c02922
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Abstract
An operationally simple organocatalytic method generates a chiral tertiary/quaternary stereocenter at the C3 position of pyrroles. The process proceeds through an amine-catalyzed direct aldol reaction of succinaldehyde with various acceptor carbonyls, followed by a Paal-Knorr reaction with a primary amine in the same pot.
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proposed reaction pathway
Key Words
Organocatalysis, Pyrroles, Paal-Knorr Pyrrole Synthesis
ID: J54-Y2022
