A convenient route to enantiopure 3-aryl-2,3-diaminopropanoic acids by diastereoselective Mannich reaction of camphor-based tricyclic iminolactone with imines.
A novel and convenient route to the asymmetric synthesis of 2,3-diamino acids via Mannich reaction of iminolactones 1a and 1b with N-protected imines has been achieved in good yields (up to 95%) and high diastereoselectivity (dr: >99:1). Hydrolysis of the Mannich adducts under acidic conditions furnished the desired 3-aryl-2,3-diaminopropanoic acids in good yields (up to 85%) with excellent enantiomeric excesses (99% ee).
Zhang
Huan-Huan
HH
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000, People's Republic of China.
Hu
Xiu-Qin
XQ
Wang
Xiao
X
Luo
Yong-Chun
YC
Xu
Peng-Fei
PF
D002164:Camphor / Q000737:chemistry*; D006575:Heterocyclic Compounds, 3-Ring / Q000737:chemistry*; D006868:Hydrolysis; D007097:Imines / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D008352:Mannich Bases / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D015091:beta-Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D006575:Heterocyclic Compounds, 3-Ring; D007097:Imines; D007783:Lactones; D008352:Mannich Bases; D015091:beta-Alanine; D002164:Camphor; C011757:2,3-diaminopropionic acid