by Marta
G. Núñez, Alistair J. M. Farley and Darren J. Dixon*
The design, synthesis, and development of a
new class of modular, strongly basic, and tunable bifunctional Brønsted
base/H-bond-donor organocatalysts are reported. These catalysts incorporate a
triaryliminophosphorane as the Brønsted basic moiety and are readily
synthesized via a last step Staudinger reaction of a chiral organoazide and a triarylphosphine.
Their application to the first general enantioselective organocatalytic
nitro-Mannich reaction of nitromethane to unactivated ketone-derived imines
allows the enantioselective construction of β-nitroamines possessing a fully
substituted carbon atom. The reaction is amenable to multigram scale-up, and
the products are useful for the synthesis of enantiopure 1,2-diamine and
α-amino acid derivatives.
Journal of the American Chemical Society
Publication Date (Web): October 9, 2013
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