Highly enantioselective allylation of alpha-ketoesters catalyzed by N,N'-dioxide-In(III) complexes.
An efficient asymmetric allylation of alpha-ketoesters was catalyzed by the N,N'-dioxide-In(III) complex in excellent yields (up to 99%) and high enantioselectivities (up to 94% ee) for a variety of substrates under mild reaction conditions. On the basis of experimental results, a possible catalytic cycle including a transition state has been proposed to explain the origin of the reactivity and asymmetric inductivity, and a bifunctional catalysis was described with Lewis base N-oxide activating tetraallylstannane and Lewis acid indium activating alpha-ketoester.
Zheng
Ke
K
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China.
Qin
Bo
B
Liu
Xiaohua
X
Feng
Xiaoming
X
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D007204:Indium / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D004952:Esters; D007659:Ketones; D009942:Organometallic Compounds; D010087:Oxides; D007204:Indium