American Chemical Society
jo7b02962_si_004.cif (2.31 MB)

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

Download (2.31 MB)
posted on 2018-01-15, 00:00 authored 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.