ISSN : 0970 - 020X, ONLINE ISSN : 2231-5039
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Abstract

Facially Selective Oxo-Diels-Alder Cycloadditions of α-Dienyl-β-Lactam: An Entry to Pyrano Tethered β-Lactams Bifunctional Hybrids

Maninderjeet Kaur Mann, Rupesh Kumar* and Gaurav Bhargava

DOI : http://dx.doi.org/10.13005/ojc/380334


Abstract:

The functionalization of -lactams at C-3 position are useful for the strategic improvement in both the dimensions, namely synthetic utility, as versatile intermediate in organic synthesis and biological potential of these heterocyclic systems. The present manuscript involved the -facial selective synthesis -lactam hybrids employing highly regioselective and diastereoselective oxo-Diels–Alder reactions of diethyl ketomalonate with -dienyl--lactam with stereocentres at its - and - positions. This protocol provided the cycloaddition of - and - stereocentric diene with symmetrical heterodienophiles forming biologically potent regioselective and diastereoselective -lactams substituted pyrano bifunctional hybrids in good yields and -facially selectivity.

Keywords:

Diastereoselective synthesis; β-lactams; Dienyl-β-lactams; π-facial selective synthesis; Regioselective synthesis

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