C2-symmetric N,N′-bis(terpenyl)ethylenediamines—synthesis and application in the enantioselective nitroaldol reaction?

RSC Advances Pub Date: 2014-03-07 DOI: 10.1039/C4RA00193A

Abstract

Optically pure C2-symmetric chiral diamines, have been synthesized by the reaction of terpenylamines with diethyloxalate, followed by the reduction of diamide with BH3–BF3. The methodology has been successfully applied and high yields achieved in the synthesis of chiral diamines derived from terpenes such as α-pinene, β-pinene, and 2-iso- and 4-carenes. These chiral diamines are found to be to be highly effective in inducing chirality in the nitroaldol reaction.

Graphical abstract: C2-symmetric N,N′-bis(terpenyl)ethylenediamines—synthesis and application in the enantioselective nitroaldol reaction
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