Highly diastereoselective switchable enantioselective Mannich reaction of glycine derivatives with imines.
Tuning of diastereoselectivity was realized in the Mannich reaction of glycine derivatives with aromatic and aliphatic N-Ts imines using CuClO4-FcPHOX ligand 4b and 4f having an MeO group at the 4-position and F atom at the 3,5-position of the phenyl ring on the P-atom respectively as catalyst, providing either anti- or syn-alpha,beta-diamino acid derivatives in high yields and in high diastereo- and enantioselectivities.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.
Xiao-Xia
XX
Yan
Qian
Q
Peng
Qing
Q
Li
Kai
K
Zhang
Jun
J
Yao
Xue-Long
XL
Hou
Yun-Dong
YD
Wu
D000596:Amino Acids / Q000138:chemical synthesis*; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D013237:Stereoisomerism; D014961:X-Ray Diffraction
D000596:Amino Acids; D007097:Imines; D005998:Glycine