Diastereoselective Synthesis of and Mechanistic Understanding for the Formation of 2-Piperidinones from Imines and Cyano-Substituted Anhydrides
2-Piperidinones are synthesized in a single step from imines and 2-cyano glutaric anhydrides. The reaction provides the products in good diastereoselectivity and generates a quaternary stereogenic center. Substitutions on the anhydride skeleton are well tolerated to provide 2-piperidinones with three stereogenic centers from a single transformation. The pertinent transition structures have also been computed using quantum mechanics and reveal the key interactions controlling the stereochemical outcome of the reaction.
Di Maso, Michael J.,Snyder, Kevin M.,De Souza Fernandes, Fábio,Pattawong, Ommidala,Tan, Darlene Q.,Fettinger, James C.,Cheong, Paul Ha-Yeon,Shaw, Jared T.
p. 4794 - 4801
(2016/04/05)
Rhodium-Catalyzed Michael Additions of Activated Nitriles to α,β - Unsaturated Esters
The Michael additions of activated nitriles to methyl acrylate (MA) and methyl vinyl ketone (MVK) proceeds with fair-to-high yields (46-92percent) in the presence of catalytic amount of HRh(CO)(PPh3)3 1 under mild reaction conditions.Key Words: Michael ad
Paganelli, Stefano,Schionato, Alberto,Botteghi, Carlo
p. 2807 - 2810
(2007/10/02)
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