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Diversity-Oriented Approach to N-Heterocyclic Compounds from alpha-Phenyl-beta-enamino Ester via a Mitsunobu-Michael Reaction Sequence

Khan, Hina P A and Chakraborty, Tushar Kanti (2018) Diversity-Oriented Approach to N-Heterocyclic Compounds from alpha-Phenyl-beta-enamino Ester via a Mitsunobu-Michael Reaction Sequence. In: JOURNAL OF ORGANIC CHEMISTRY, 83 (4). pp. 2027-2039.

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Official URL: http://dx.doi.org/10.1021/acs.joc.7b02962

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 alpha-phenyl-beta-enamino ester. The reaction sequence relies on the unexplored reactivity of alpha-phenyl-beta-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.

Item Type: Journal Article
Additional Information: Copy right for the article belong toAMER CHEMICAL SOC, 1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 03 Apr 2018 18:27
Last Modified: 03 Apr 2018 18:27
URI: http://eprints.iisc.ac.in/id/eprint/59463

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