Diversity-Oriented Approach to N-Heterocyclic Compounds from α-Phenyl-ß-enamino Ester via a Mitsunobu-Michael Reaction Sequence.
J Org Chem
; 83(4): 2027-2039, 2018 02 16.
Article
em En
| MEDLINE
| ID: mdl-29334224
ABSTRACT
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-ß-enamino ester. The reaction sequence relies on the unexplored reactivity of α-phenyl-ß-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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MEDLINE
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En
Ano de publicação:
2018
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Article