Reaction of alpha-(N-carbamoyl)alkylcuprates with enantioenriched propargyl electrophiles: synthesis of enantioenriched 3-pyrrolines.
Enantioenriched propargyl mesylates or perfluorobenzoates react with alpha-(N-carbamoyl)alkylcuprates to afford scalemic alpha-(N-carbamoyl) allenes which undergo N-Boc deprotection and AgNO3-promoted cyclization to afford N-alkyl-3-pyrrolines. The synthetic sequence proceeds under optimal conditions with no loss of enantiopurity relative to the starting propargyl alcohols prepared by asymmetric addition of terminal alkynes to aldehydes.
Dieter
R Karl
RK
Howard L. Hunter Chemistry Laboratory, Clemson University, Clemson, South Carolina 29634-0973, USA. dieterr@clemson.edu
Chen
Ningyi
N
Gore
Vinayak K
VK
D001565:Benzoates / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D001565:Benzoates; D008698:Mesylates; D009942:Organometallic Compounds; D011758:Pyrroles; D003300:Copper