Stereoselective allyl amine synthesis through enantioselective addition of diethylzinc and [1,3]-chirality transfer: synthesis of lentiginosine and polyoxamic acid derivative.
A new synthetic method for the preparation of allyl amines has been developed. The key steps of this method are enantioselective addition of diethylzinc and [1,3]-chirality transfer through the [3.3] sigmatropic rearrangement of allyl cyanates. Stereocontrolled syntheses of lentiginosine (1) and polyoxamic acid derivative 2 from a common intermediate 7 derived from D-tartaric acid (8), have been accomplished.
Ichikawa
Yoshiyasu
Y
Faculty of Science, Kochi University, Akebono-cho, Kochi 780-8520, Japan. ichikawa@cc.kochi-u.ac.jp
Ito
Takashi
T
Isobe
Minoru
M
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D001383:Azetidinecarboxylic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010072:Oxamic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D000498:Allyl Compounds; D000588:Amines; D009942:Organometallic Compounds; C063984:lentiginosine; C010624:polyoximic acid; D001383:Azetidinecarboxylic Acid; D010072:Oxamic Acid; C454811:diethylzinc