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Enantioselective Direct Synthesis of C3-Hydroxyalkylated Pyrrole via an Amine-Catalyzed Aldol/Paal–Knorr Reaction Sequence
(ACS, 2022-10) Kumar, Indresh
Creating functionality with chirality at position C3 of pyrrole is challenging. An operationally simple organocatalytic method has been developed to generate functionality with a chiral tertiary/quaternary stereocenter at position C3 of pyrrole. 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. A series of chiral C3-hydroxyalkylated N-alkyl/Ar/H-pyrroles have been synthesized for the first time with good to high yields and excellent enantioselectivity.
One-Pot Synthesis of Chiral Tetracyclic Dibenzo[ b, f][1,4]oxazepine-Fused 1,2-Dihydropyridines (DHPs) under Metal-Free Conditions
(ACS, 2018-06) Kumar, Indresh
An efficient protocol for the catalytic asymmetric synthesis of new dibenzo[b,f][1,4]-oxazepine-fused 1,2-dihydropyridines (DHPs) has been described under metal-free conditions. This reaction proceeds through proline-catalyzed direct Mannich/cyclization between seven-membered dibenzo[b,f][1,4]-oxazepine-imines and aqueous glutaraldehyde, followed by IBX-mediated site-selective dehydrogenative oxidation in one-pot operation with high yields (up to 92%) and excellent enantioselectivity (up to >99:1 er).