title: Design, synthesis, and applications of chiral N-2-phenyl-2-propyl sulfinyl imines for group-assisted purification (GAP) asymmetric synthesis.
abstract: A new chiral (Rs)-2-phenyl-2-propyl sulfinamide has been designed and synthesized; its derived aldimines and ketimines have been applied for asymmetric addition reaction with allylmagnesium bromide. The reaction was conveniently performed at room temperature to give a series of homoallylic amines in high yields (up to quant) and diastereoselectivity (up to >99% de). The pure products were obtained by relying on group-assisted purification (GAP) chemistry to avoid traditional purification methods of column chromatography or recrystallization. The conversion of disulfide to (R(s))-thiosulfinate which contains a newly generated polar group was also confirmed to be of the GAP chemistry in which washing crude product can generate pure enantiomer. The absolute stereochemistry has been determined by X-ray analysis.
authors.affiliation: Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA.
authors.forename: Suresh
authors.initials: S
authors.lastname: Pindi
authors.forename: Jianbin
authors.initials: J
authors.lastname: Wu
authors.forename: Guigen
authors.initials: G
authors.lastname: Li
mesh_terms: D018360:Crystallography, X-Ray; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: C582741:2-phenyl-2-propyl sulfinamide; D007097:Imines; D009570:Nitriles; D013452:Sulfonium Compounds; C542835:ketimine