Highly diastereoselective addition of the lithium enolate of alpha-diazoacetoacetate to N-sulfinyl imines: enantioselective synthesis of 2-oxo and 3-oxo pyrrolidines.
The highly enantioselective synthesis of 2-oxo and 3-oxo pyrrolidines has been achieved by diastereoselective addition of the lithium enolate of alpha-diazoacetoacetate to chiral N-sulfinyl imines, followed by photoinduced Wolff rearrangement or Rh(II)-catalyzed intramolecular N-H insertion.
Dong
Changqing
C
Beijing National Laboratory of Molecular Sciences and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China.
Mo
Fanyang
F
Wang
Jianbo
J
D000085:Acetates / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D008958:Models, Molecular; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000085:Acetates; D007097:Imines; D011759:Pyrrolidines; D008094:Lithium