Enantioselective allylation of imines catalyzed by newly developed (?)-β-pinene-based π-allylpalladium catalyst: an efficient synthesis of (R)-α-propylpiperonylamine and (R)-pipecolic acid??

Organic & Biomolecular Chemistry Pub Date: 2012-07-26 DOI: 10.1039/C2OB26188J

Abstract

A newly developed π-allylpalladium with a (?)-β-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)-α-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.

Graphical abstract: Enantioselective allylation of imines catalyzed by newly developed (?)-β-pinene-based π-allylpalladium catalyst: an efficient synthesis of (R)-α-propylpiperonylamine and (R)-pipecolic acid
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