An asymmetric aerobic aza-Wacker-type cyclization: synthesis of isoindolinones bearing tetrasubstituted carbon stereocenters.
It's all in the solvent: An enantioselective variant of an aza-Wacker-type cyclization that gives isoindolinones containing tetrasubstituted carbon centers α to the nitrogen atom has been developed (see scheme; tfa=trifluoroacetate). The use of a highly coordinating solvent is crucial for the activity of the catalyst and the stereoselectivity the reaction (up to 99 % ee).
School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, China.
Guoqiang
G
Yang
Chaoren
C
Shen
Wanbin
W
Zhang
D000586:Amination; D001372:Aza Compounds / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D054833:Isoindoles / Q000138:chemical synthesis / Q000737:chemistry*; D008968:Molecular Conformation; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
D001372:Aza Compounds; C110621:Isoindol-1-one; D054833:Isoindoles; D010165:Palladium; D002244:Carbon