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.
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]
Ichikawa
Yoshiyasu
Y
Faculty of Science, Kochi University, Akebono-cho, Kochi 780-8520, Japan. ichikawa@kochi-u.ac.jp
Egawa
Haruka
H
Ito
Takashi
T
Isobe
Minoru
M
Nakano
Keiji
K
Kotsuki
Hiyoshizo
H
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
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