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Rhodium(II)‐Catalyzed Highly Stereoselective C3 Functionalization of Indolizines with N ‐Sulfonyl‐1,2,3‐triazoles
Author(s) -
Kahar Nilesh Machhindra,
Nabar Kasturi Uday,
Jadhav Pankaj Pandit,
Dawande Sudam Ganpat
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201800631
Subject(s) - chemistry , surface modification , stereoselectivity , regioselectivity , sulfonyl , rhodium , indolizine , catalysis , combinatorial chemistry , organic chemistry , medicinal chemistry , alkyl
An efficient and highly stereoselective approach for the C3 functionalization of indolizines through rhodium(II)‐catalyzed insertion of aza‐vinyl carbenes to synthesize N ‐sulfonylamine alkenyl derivatives of indolizines is disclosed. Variably functionalized indolizines underwent C3 functionalization to afford moderate to good yields. Under similar reaction conditions pyrrolo[1,2‐a]quinolines resulted in regioselective C1 functionalization to give their N ‐sulfonylamine alkenyl derivatives. The reaction methodology was successfully extended for the preparation of 1,3‐bis( N ‐sulfonylamine alkenyl)indolizine derivatives and C3‐functionalized indolizines were used for the preparation of new molecular entities.