Diastereo- and enantioselective synthesis of alpha,gamma-diaminobutyric acid derivatives via Cu-catalyzed asymmetric Michael reaction.
The first highly diastereo- and enantioselective catalytic asymmetric Michael addition of glycine derivatives to nitroalkenes have been developed. The enantioselectivity of ortho-substituted products can be significantly improved by using a new 1,2-P,N-ferrocene ligand L5. The alpha,gamma-diaminoacid derivative was obtained without the loss of optical activity from the adduct.
Li
Qing
Q
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.
Ding
Chang-Hua
CH
Hou
Xue-Long
XL
Dai
Li-Xin
LX
D000613:Aminobutyrates / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D005296:Ferrous Compounds / Q000737:chemistry; D008024:Ligands; D000075163:Metallocenes; D013237:Stereoisomerism; D013379:Substrate Specificity
D000613:Aminobutyrates; D005296:Ferrous Compounds; D008024:Ligands; D000075163:Metallocenes; C005959:2,4-diaminobutyric acid; D003300:Copper; C004998:ferrocene