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A new asymmetric activation strategy for hydrazones as acyl anion equivalents in the bimetallic catalyzed carbonyl-ene reaction

Organic and Biomolecular Chemistry, ISSN: 1477-0520, Vol: 19, Issue: 9, Page: 2055-2062
2021
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A new asymmetric activation strategy for hydrazones as acyl anion equivalents is developed in the bimetallic catalyzed carbonyl-ene reaction of isatins and hydrazones. Under mild conditions, optically active functionalized 3-hydroxy-2-oxindoles were furnished in up to 98% yield with up to 97% enantioselectivity. In this process, formaldehydetert-butylhydrazone which is seldom employed in asymmetric carbonyl-ene reactions accelerated by a metallic catalyst can be activated well by a Brønsted base. A possible catalytic cycle is proposed.

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