Bifunctional guanidine via an amino amide skeleton for asymmetric Michael reactions of beta-ketoesters with nitroolefins: a concise synthesis of bicyclic beta-amino acids.
Two activations are better than one: The chiral bifunctional guanidine 1, which features an amino amide backbone, catalyzes the asymmetric Michael addition of a range of substrates and gives products with excellent stereoselectivities. The method also allows the efficient synthesis of optically pure beta-amino acid esters. Both the guanidine group and the NH proton of the amide were important for the dual activation.
Yu
Zhipeng
Z
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, PR China.
Liu
Xiaohua
X
Zhou
Lin
L
Lin
Lili
L
Feng
Xiaoming
X
D000475:Alkenes / Q000737:chemistry; D000577:Amides / Q000737:chemistry*; D000598:Amino Acids, Cyclic / Q000138:chemical synthesis / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004952:Esters; D019791:Guanidine / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D000577:Amides; D000598:Amino Acids, Cyclic; D001643:Bridged Bicyclo Compounds; D004952:Esters; D019791:Guanidine