Enantioselective Allylation of Ketones Catalyzed by N,N′‐Dioxide and Indium(III) Complex.

作者：Xin Zhang; Donghui Chen; Xiaohua Liu; Xiaoming Feng

来源：ChemInform, 2007, 38(49): 5227-5233.

DOI：10.1002/chin.200749036

Complexes of (S')-pipecolic acid-, L-proline-, and other amino acid-derived TVyV'-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 Ll-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.

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  四川大学