Organic Chemistry Portal



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:

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

see article for more reactions


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.

see article for more examples

proposed reaction pathway

Key Words

Organocatalysis, Pyrroles, Paal-Knorr Pyrrole Synthesis

ID: J54-Y2022