Functionalization of alpha,beta-unsaturated esters and ketones: a facile and highly stereoselective one-pot approach to N-protected alpha,beta-dehydroamino acid derivatives.
A new, facile, and highly stereoselective protocol toward alpha,beta-dehydroamino acid derivatives has been developed. The one-pot synthesis was very convenient to perform by using the aminohalogenation reaction of alpha,beta-unsaturated esters and ketones followed by treatment with specific bases. Only two [2.2.2] bicyclic organic bases were found to be effective for this transformation. Good yields (58-68%) and excellent Z-selectivity were obtained for 12 examples. [reaction: see text]
Chen
Dianjun
D
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA.
Guo
Li
L
Liu
Junying
J
Kirtane
Sameer
S
Cannon
John F
JF
Li
Guigen
G
D000596:Amino Acids / Q000032:analysis / Q000138:chemical synthesis*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004952:Esters; D007202:Indicators and Reagents; D007659:Ketones / Q000737:chemistry*; D013237:Stereoisomerism
D000596:Amino Acids; D004952:Esters; D007202:Indicators and Reagents; D007659:Ketones