Journal
ORGANIC LETTERS
Volume 24, Issue 41, Pages 7549-7554Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02922
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Funding
- BITS Pilani
- DST-SERB, New Delhi
- DST- SERB, New Delhi [CRG-2020/003424]
- DST-FIST [SR/FST/CSI-270/2015]
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An operationally simple organocatalytic method has been developed to create functionality with a chiral tertiary/quaternary stereocenter at position C3 of pyrrole. The synthesized chiral C3-hydroxyalkylated N-alkyl/Ar/H-pyrroles showed good to high yields and excellent enantioselectivity.
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.
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