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Updated: Jun 16, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Asymmetric allylation, crotylation, and cinnamylation of N-heteroaryl hydrazones
Miriam Inbar Feske1, Alexander Buitrago Santanilla, James L Leighton
1Department of Chemistry, Columbia University, New York, New York 10027, USA.
Abstract:
A new class of N-heteroaryl hydrazones has been developed as an alternative to N-acylhydrazones and 2-aminophenol-derived imines in asymmetric allylation, crotylation, and cinnamylation reactions with chiral allylchlorosilanes. The hydrazones are readily and inexpensively prepared, perform well in the allylation chemistry, and more importantly, the product hydrazides may be smoothly reduced by Pd(OH)(2)-catalyzed hydrogenation to reveal the corresponding amine products.
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