1100077-11-9Relevant articles and documents
Controlling stereoselectivity in the aminocatalytic enantioselective mannich reaction of aldehydes with in situ generated N-carbamoyl imines
Galzerano, Patrizia,Agostino, Dario,Bencivenni, Giorgio,Sambri, Letizia,Bartoli, Giuseppe,Melchiorre, Paolo
experimental part, p. 6069 - 6076 (2010/09/07)
A simple and convenient method for the direct, aminocatalytic, and highly enantioselective Mannich reactions of aldehydes with in situ generated N-carbamoyl imines has been developed. Both α-imino esters and aromatic imines serve as suitable electrophilic components. Moreover, the judicious selection of commercially available secondary amine catalysts allows selective access to the desired stereoisomer of the N-tert-butoxycarbonyl (Boc) or N-carbobenzyloxy (Cbz) Mannich adducts, with high control over the syn or anti relative configura-tion and almost perfect enantioselectivity. Besides the possibility to fully control the stereochemistry of the Mannich reaction, the main advantage of this method lies in the operational simplicity; the highly reactive N-carbamate-protected imines are generated in situ from stable and easily handled aamido sulfones. 2010 Wiley-VCH Verlag GmbH & Co. KGaA.
Aminocatalytic enantioselective anti-mannich reaction of aldehydes with in situ generated N-cbz and N-boc imines
Gianelli, Chiara,Sambri, Letizia,Carlone, Armando,Bartoli, Giuseppe,Melchiorre, Paolo
supporting information; experimental part, p. 8700 - 8702 (2009/05/15)
(Chemical Equation Presented) The title reaction catalyzed by the commercially available chiral secondary amine 1 proceeds with high stereocontrol and allows the in situ generation of N-carbamate-protected imines from stable a-amido sulfones 2. This organocatalytic approach provides easy and convenient access to valuable compounds 3 in high yield, with very good anti selectivity,and in high enantiomeric purity.
