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Enantioselective allylation of imines catalyzed by newly developed (-)-beta-pinene-based pi-allylpalladium catalyst: an efficient synthesis of (R)-alpha-propylpiperonylamine and (R)-pipecolic acid

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Title Enantioselective allylation of imines catalyzed by newly developed (-)-beta-pinene-based pi-allylpalladium catalyst: an efficient synthesis of (R)-alpha-propylpiperonylamine and (R)-pipecolic acid
 
Creator FERNANDES, RA
NALLASIVAM, JL
 
Subject BEARING DIPHOSPHINIDENECYCLOBUTENE LIGANDS
HIGHLY STEREOSELECTIVE-SYNTHESIS
ALPHA-AMINO-ACIDS
ASYMMETRIC ALLYLATION
HOMOALLYLIC AMINES
ORGANOMETALLIC REAGENTS
ALLYLIC ALKYLATION
N-ACYLHYDRAZONES
ACTIVE CATALYSTS
METAL-COMPOUNDS
 
Description A newly developed pi-allylpalladium with a (-)-beta-pinene framework and an isobutyl side chain catalyzed the enantioselective allylation of imines in good yields and enantioselectivities (20 examples, up to 98% ee). An efficient enantioselective synthesis of the (R)-alpha-propyl piperonylamine part of DMP 777, a human leukocyte elastase inhibitor and (R)-pipecolic acid have been achieved as a useful application of this methodology.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2014-10-16T14:02:17Z
2014-10-16T14:02:17Z
2012
 
Type Article
 
Identifier ORGANIC & BIOMOLECULAR CHEMISTRY, 10(38)7789-7800
http://dx.doi.org/10.1039/c2ob26188j
http://dspace.library.iitb.ac.in/jspui/handle/100/15733
 
Language en