title: Magnesium-tartramide complex mediated asymmetric Strecker-type reaction of nitrones using cyanohydrin.
abstract: An asymmetric Strecker-type reaction of nitrones using acetone cyanohydrin as a source of HCN has been realized. A magnesium-tartramide complex, generated from (R,R)-2,3-dihydroxy-1,4-di(pyrrolidin-1-yl)-butane-1,4-dione and MeMgBr, promoted transcyanation from the bromomagnesium salt of the cyanohydrin, in the presence of a catalytic amount of DBU, to afford the corresponding optically active (S)-α-amino nitrile derivatives. The reaction was applicable to various nitrones giving high-to-excellent enantioselectivities.
authors: Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University , Kakuma, Kanazawa, Ishikawa 920-1192, Japan.
authors: Takahiro
authors: T
authors: Sakai
authors: Takahiro
authors: T
authors: Soeta
authors: Kohei
authors: K
authors: Endo
authors: Shuhei
authors: S
authors: Fujinami
authors: Yutaka
authors: Y
authors: Ukaji
mesh_terms: D002384:Catalysis; D008274:Magnesium / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D009589:Nitrogen Oxides / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D009570:Nitriles; D009589:Nitrogen Oxides; D009942:Organometallic Compounds; C430593:cyanohydrin; C015388:nitrones; C010833:acetone cyanohydrin; D008274:Magnesium