Enantioselective conjugate addition of N,N-dialkylhydrazones to alpha-hydroxy enones.
The activation of alpha-hydroxy enones by the Zn(OTf)2/tBuBOX catalyst enables the enantioselective conjugate addition of 1-methyleneaminopyrrolidine as a neutral d1 synthon. Experimental evidence supports a stereochemical model where a triflate ligand controls the geometry of the catalyst-substrate complex by means of a OH-OTf hydrogen bond. The synthesis of beta-cyano acids illustrates the potential of the methodology.
Monge
David
D
Instituto de Investigaciones Químicas CSIC-US, Américo Vespucio 49, E-41092 Seville, Spain.
Martín-Zamora
Eloísa
E
Vazquez
Juan
J
Alcarazo
Manuel
M
Alvarez
Eleuterio
E
Fernandez
Rosario
R
Lassaletta
José M
JM