title: Stereocontrolled route to vicinal diamines by [3.3] sigmatropic rearrangement of allyl cyanate: asymmetric synthesis of anti-(2R,3R)- and syn-(2R,3S)-2,3-diaminobutanoic acids.
abstract: A stereocontrolled route via allyl 1,2-diols to vicinal diamines based on the [3.3] sigmatropic rearrangement of allyl cyanate has been developed. Our approach consists of two consecutive steps: stereoselective construction of allyl anti- and syn-1,2-diols followed by [1,3]-chirality transfer by sigmatropic rearrangement, which allow an access to anti-(2R,3R)- and syn-(2R,3S)-2,3-diaminobutanoic acids. [reaction: see text]
authors.affiliation: Faculty of Science, Kochi University, Akebono-cho, Kochi 780-8520, Japan. ichikawa@kochi-u.ac.jp
authors.forename: Yoshiyasu
authors.initials: Y
authors.lastname: Ichikawa
authors.forename: Haruka
authors.initials: H
authors.lastname: Egawa
authors.forename: Takashi
authors.initials: T
authors.lastname: Ito
authors.forename: Minoru
authors.initials: M
authors.lastname: Isobe
authors.forename: Keiji
authors.initials: K
authors.lastname: Nakano
authors.forename: Hiyoshizo
authors.initials: H
authors.lastname: Kotsuki
mesh_terms: D000079:Acetaldehyde / Q000737:chemistry; D000498:Allyl Compounds / Q000737:chemistry*; D000613:Aminobutyrates / Q000138:chemical synthesis*; D003959:Diamines / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D017953:Isocyanates / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D008968:Molecular Conformation; D063065:Organophosphonates / Q000737:chemistry; D019163:Reducing Agents; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D000613:Aminobutyrates; D003959:Diamines; D007202:Indicators and Reagents; D017953:Isocyanates; D007659:Ketones; D063065:Organophosphonates; D019163:Reducing Agents; C491149:allyl isocyanate; C522314:2,3-diaminobutanoic acid; D000079:Acetaldehyde