Chiral Brønsted acid catalyzed enantioselective addition of alpha-isocyanoacetamides to aldehydes.
A clean and highly efficient enantioselective addition of alpha-isocyanoacetamides to aliphatic aldehydes catalyzed by chiral phosphoric acid in the presence of MS 5 A in toluene at -40 degrees C was developed. Excellent yields (85-98%) and good to excellent enantioselectivities (up to >99% ee) were achieved.
Zeng
Xiaofei
X
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singapore.
Ye
Kehan
K
Lu
Min
M
Chua
Pei Juan
PJ
Tan
Bin
B
Zhong
Guofu
G
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010756:Phosphoric Acids / Q000737:chemistry*; D013237:Stereoisomerism; D014050:Toluene / Q000737:chemistry
D000447:Aldehydes; D009570:Nitriles; D010756:Phosphoric Acids; D014050:Toluene; C031594:2-cyanoacetamide