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

作者: Subhabrata Sen , Siva R Kamma , Rambabu Gundla , Uma Adepally , Santosh Kuncha

DOI: 10.1039/C2RA22115B

关键词:

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

参考文章(51)
Eugene E. Van Tamelen, Rodger L. Foltz, Biogenetic-type synthesis of lupin alkaloids Journal of the American Chemical Society. ,vol. 91, pp. 7372- 7377 ,(1969) , 10.1021/JA01054A026
Hassan Pajouhesh, George R. Lenz, Medicinal chemical properties of successful central nervous system drugs. Neurorx. ,vol. 2, pp. 541- 553 ,(2005) , 10.1602/NEURORX.2.4.541
David A. Evans, Thomas C. Britton, Roberta L. Dorow, Joseph F. Dellaria, The asymmetric synthesis of α-amino and α-hydrazino acid derivatives via the stereoselective amination of chiral enolates with azodicarboxylate esters Tetrahedron. ,vol. 44, pp. 5525- 5540 ,(1988) , 10.1016/S0040-4020(01)86058-0
Jen Chen, Leslie J. Browne, Nina C. Gonnela, Total synthesis of (±)-matrine Journal of The Chemical Society, Chemical Communications. pp. 905- 907 ,(1986) , 10.1039/C39860000905
Roger M. Smith, Pipermethystine, a novel pyridone alkaloid from piper methysticum Tetrahedron. ,vol. 35, pp. 437- 439 ,(1979) , 10.1016/0040-4020(79)80084-8
Dhevalapally B. Ramachary, Chintalapudi Venkaiah, Y. Vijayendar Reddy, Mamillapalli Kishor, Multi-catalysis cascade reactions based on the methoxycarbonylketene platform: diversity-oriented synthesis of functionalized non-symmetrical malonates for agrochemicals and pharmaceuticals Organic and Biomolecular Chemistry. ,vol. 7, pp. 2053- 2062 ,(2009) , 10.1039/B901652J
Roger M. Smith, Kava lactones in Piper methysticum from fiji Phytochemistry. ,vol. 22, pp. 1055- 1056 ,(1983) , 10.1016/0031-9422(83)85065-1
Warren R. J. D. Galloway, Andreas Bender, Martin Welch, David R. Spring, The Discovery of Antibacterial Agents Using Diversity-Oriented Synthesis Chemical Communications. pp. 2446- 2462 ,(2009) , 10.1039/B816852K
Miles Congreve, Robin Carr, Chris Murray, Harren Jhoti, A 'rule of three' for fragment-based lead discovery? Drug Discovery Today. ,vol. 8, pp. 876- 877 ,(2003) , 10.1016/S1359-6446(03)02831-9