title: Asymmetric halo-Mannich-type reaction provides access to pyrrolidines and beta-proline derivatives.
abstract: [reaction: see text] A new halo-Mannich-type reaction is reported using cyclopropyl carbonyl-derived enolates and sulfonyl-protected imines. Chiral oxazolidinones auxiliaries were found to be effective for completely controlling the stereochemistry of the products. Variations in the oxazolidinone, protecting group, and imine components show this to be a quite general reaction. The initial iodo-Mannich products were found to be readily cyclized in the presence of triethylamine to afford the resulting protected pyrrolidines, which could be readily deprotected under standard conditions.
authors.affiliation: Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA.
authors.forename: Cody
authors.initials: C
authors.lastname: Timmons
authors.forename: Li
authors.initials: L
authors.lastname: Guo
authors.forename: Junying
authors.initials: J
authors.lastname: Liu
authors.forename: John F
authors.initials: JF
authors.lastname: Cannon
authors.forename: Guigen
authors.initials: G
authors.lastname: Li
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D008352:Mannich Bases; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D011759:Pyrrolidines / Q000138:chemical synthesis*
chemical_list: D008352:Mannich Bases; D011759:Pyrrolidines; D011392:Proline; C072401:beta-proline