Zn-Catalyzed enantioselective allylation and allenylation of isatins by virtue of a proline-derived chiral ligand†
Zhenggen
Zha 
a
and
Zhiyong
Wang
*a
a
and
Zhiyong
Wang
*a
Abstract
An asymmetric allylation and allenylation of isatins with facile organoboron reagents was developed under the catalysis of a Lewis acid. A series of optically pure 3-allyl-3-hydroxyoxindoles and 3-allenyl-3-hydroxyoxindoles can be obtained in excellent yields (up to 99% yield) and high enantioselectivities (up to 97% ee). The possible transition state was supported by DFT calculation and the corresponding mechanism was proposed. A gram scale experiment and further functionalization of these chiral 3-hydroxyoxindoles are established.
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