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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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 |
|---|---|
| Publication: | JOURNAL OF ORGANIC CHEMISTRY |
| Publisher: | AMER CHEMICAL SOC, 1155 16TH ST, NW, WASHINGTON, DC 20036 USA |
| 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 |
| 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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