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Diversity-Oriented Approach to N-Heterocyclic Compounds from α‑Phenyl-β-enamino Ester via a Mitsunobu-Michael Reaction Sequence

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posted on 15.01.2018, 00:00 by Hina P. A. Khan, Tushar Kanti Chakraborty
Herein we delineate a novel route for the diastereoselective construction of diversely substituted N-heterocyclic ring systems as valuable scaffolds for natural products and pharmaceuticals, starting from an easily accessible prochiral α-phenyl-β-enamino ester. The reaction sequence relies on the unexplored reactivity of α-phenyl-β-enamino ester as a nucleophilic partner in the Mitsunobu reaction to forge the N-tethered alkene–alcohol/thiol/amine intermediate, which was subjected to an intramolecular hetero-Michael addition reaction under mild conditions to furnish the respective N-heterocyclic compounds embedded with an exocyclic chiral center in high yields and excellent diastereoselectivities. The methodology is amenable for a broad range of substrates based on a metal-free approach.

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