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Download fileDiversity-Oriented Approach to N-Heterocyclic Compounds from α‑Phenyl-β-enamino Ester via a Mitsunobu-Michael Reaction Sequence
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posted on 2018-01-15, 00:00 authored by Hina P.
A. Khan, Tushar Kanti ChakrabortyHerein 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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exocyclic chiral centerdiastereoselective constructionheterocyclic compoundsreaction sequenceprochiral α- phenyl -β-enamino esterheterocyclic ring systemsMitsunobu reactionα- phenyl -β-enamino esternucleophilic partnerMitsunobu-Michael Reaction Sequence Hereinmetal-free approachHeterocyclic Compoundsintramolecular hetero-Michael addition reactionnovel routeDiversity-Oriented Approach