Organocatalytic sequential alpha-amination-Horner-Wadsworth-Emmons olefination of aldehydes: enantioselective synthesis of gamma-amino-alpha,beta-unsaturated esters.
A novel and highly enantioselective method for the synthesis of gamma-amino-alpha,beta-unsaturated esters via tandem alpha-amination-Horner-Wadsworth-Emmons (HWE) olefination of aldehydes is described. The one-pot assembly has been demonstrated for the construction of functionalized chiral 2-pyrrolidones, subunits present in several alkaloids. [structure: see text]
Kotkar
Shriram P
SP
Chemical Engineering and Process Development Division, National Chemical Laboratory, Pashan Road, Pune 411 008, India.
Chavan
Vilas B
VB
Sudalai
Arumugam
A
D000447:Aldehydes / Q000737:chemistry*; D000470:Alkaloids / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D004952:Esters / Q000138:chemical synthesis*; D015394:Molecular Structure; D011760:Pyrrolidinones / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000447:Aldehydes; D000470:Alkaloids; D000475:Alkenes; D000588:Amines; D004952:Esters; D011760:Pyrrolidinones; C028537:2-pyrrolidone