A rapid and general method for the asymmetric synthesis of 2-substituted pyrrolidines using tert-butanesulfinamide.
A new method for the asymmetric synthesis of 2-substituted pyrrolidines in three steps from commercially available starting materials is described. Addition of the Grignard reagent prepared from 2-(2-bromoethyl)-1,3-dioxane to N-tert-butanesulfinyl aldimines proceeds in high yields and with good diastereoselectivities. The sulfinamide products are then cleanly converted into pyrrolidines in one step.
Brinner
Kristin M
KM
Center for New Directions in Organic Synthesis, Chemistry Department, University of California, Berkeley, CA 94720, USA. kristin_brinner@chiron.com
Ellman
Jonathan A
JA
D002073:Butanes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011759:Pyrrolidines / Q000138:chemical synthesis*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013449:Sulfonamides / Q000737:chemistry*
D002073:Butanes; D011759:Pyrrolidines; D013449:Sulfonamides; C511422:tert-butanesulfinamide