Issue 7, 2013

A reagent based DOS strategy via Evans chiral auxiliary: highly stereoselective Michael reaction towards optically active quinolizidinones, piperidinones and pyrrolidinones

Abstract

In the present study, we have demonstrated the diversity oriented synthesis of nitrogen heterocycles viz. chiral piperidinones, quinolizidinones and diaryl pyrrolidinones from Michael adducts generated via a TiCl4-catalyzed highly stereoselective Michael reaction with nitrostyrenes and an Evans chiral auxiliary. We also reported a Cu-4,4’-(isopropyl)-substituted isopropylidene-bridged 2,2’-bis-1,3’-oxazoline catalyst mediated catalytic asymmetric version of this reaction. In silico analysis is utilized to evaluate the diversity of the set of compounds against shape space (PMI), polar surface area (PSA) calculations and relevant drug like properties (viz. HBA, HBD, PSA, mol. wt., log P and log D). Finally, the molecules were screened against microorganisms to assess their antimicrobial properties.

Graphical abstract: A reagent based DOS strategy via Evans chiral auxiliary: highly stereoselective Michael reaction towards optically active quinolizidinones, piperidinones and pyrrolidinones

Supplementary files

Article information

Article type
Paper
Submitted
11 Sep 2012
Accepted
12 Dec 2012
First published
13 Dec 2012

RSC Adv., 2013,3, 2404-2411

A reagent based DOS strategy via Evans chiral auxiliary: highly stereoselective Michael reaction towards optically active quinolizidinones, piperidinones and pyrrolidinones

S. Sen, S. R. Kamma, R. Gundla, U. Adepally, S. Kuncha, S. Thirnathi and U. V. Prasad, RSC Adv., 2013, 3, 2404 DOI: 10.1039/C2RA22115B

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