title: Ni-catalyzed homoallylation of polyhydroxy n,o-acetals with conjugated dienes promoted by triethylborane.
abstract: In the presence of Ni-catalyst and triethylborane, N,O-acetals prepared from glycolaldehyde and glyceraldehyde with primary amines in situ underwent homoallylation with conjugated dienes to provide 2-amino-5-hexenols in high regio- and stereoselectivity. Under similar reaction conditions, N,O-acetals from carbohydrates with primary amines provided the corresponding polyhydroxy-bishomoallylamines in good to reasonable yields.
authors.affiliation: Graduate School of Engineering, Nagasaki University, 1-14, Bunkyo machi, Nagasaki 852-8521, Japan.
authors.forename: Takamichi
authors.initials: T
authors.lastname: Mori
authors.affiliation: Graduate School of Engineering, Nagasaki University, 1-14, Bunkyo machi, Nagasaki 852-8521, Japan.
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Akioka
authors.affiliation: Graduate School of Engineering, Nagasaki University, 1-14, Bunkyo machi, Nagasaki 852-8521, Japan.
authors.forename: Gen
authors.initials: G
authors.lastname: Onodera
authors.affiliation: Graduate School of Engineering, Nagasaki University, 1-14, Bunkyo machi, Nagasaki 852-8521, Japan. manasari@nagasaki-u.ac.jp.
authors.forename: Masanari
authors.initials: M
authors.lastname: Kimura
mesh_terms: D000080:Acetals / Q000138:chemical synthesis*; D001880:Boranes / Q000737:chemistry*; D002070:Butadienes / Q000737:chemistry; D002384:Catalysis; D045782:Hemiterpenes / Q000737:chemistry; D009532:Nickel / Q000737:chemistry*; D010420:Pentanes / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D001880:Boranes; D002070:Butadienes; D045782:Hemiterpenes; D010420:Pentanes; C005059:isoprene; D009532:Nickel; C079756:triethylborane