Intramolecular carbolithiation reactions for the preparation of 3-alkenylpyrrolidines.
Tin-lithium exchange allows the formation of alpha-amino-organolithium species that undergo anionic cyclization onto allylic ethers to give 3-alkenylpyrrolidines. The methodology has been applied to the synthesis of an advanced intermediate related to the natural product (-)-alpha-kainic acid.
Coldham
Iain
I
School of Chemistry, University of Exeter, Stocker Road, Exeter, UK EX4 4QD. i.coldham@ex.ac.uk
Price
Kathy N
KN
Rathmell
Richard E
RE
D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D007608:Kainic Acid / Q000138:chemical synthesis; D008094:Lithium / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014001:Tin / Q000737:chemistry
D000475:Alkenes; D009942:Organometallic Compounds; D011759:Pyrrolidines; D014001:Tin; D008094:Lithium; D007608:Kainic Acid