Enantioselective allylation of ketones catalyzed by N,N'-dioxide and indium(III) complex.
Complexes of (S)-pipecolic acid-, L-proline-, and other amino acid-derived N,N'-dioxides coordinated with different metal ions have been investigated in the enantioselective allylation of ketones. A variety of aromatic ketones were found to be suitable substrates in the presence of the L1-In(III) complex, and afforded the corresponding homoallylic alcohols with good enantioselectivites (up to 83% ee) and moderate to high yields (up to 94%). On the basis of the 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 catalyst was described with Lewis base N-oxide activating tetraallyltin and Lewis acid indium activating ketone.
Zhang
Xin
X
Key Laboratory of Green Chemistry & Technology (Sichuan University), Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China.
Chen
Donghui
D
Liu
Xiaohua
X
Feng
Xiaoming
X
D002384:Catalysis; D007204:Indium / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D010087:Oxides / Q000737:chemistry*; D013237:Stereoisomerism; D013696:Temperature
D007659:Ketones; D008024:Ligands; D010087:Oxides; D007204:Indium