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Dynamic kinetic asymmetric allylation of hydrazines and hydroxylamines.

Organic letters (2009-07-11)
Ian Mangion, Neil Strotman, Michael Drahl, Jason Imbriglio, Erin Guidry
ABSTRACT

Hydrazines and hydroxylamines have been found to be excellent nucleophiles for the palladium-catalyzed dynamic asymmetric allylic amination of vinyl epoxide, with good yields and enantioselectivities of up to 97% ee. This method is applicable to acyclic and heterocyclic amines and was applied toward a five-step synthesis of (R)-piperazic acid.

MATERIALS
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Brand
Product Description

Sigma-Aldrich
3-Hydroxy-5-methylisoxazole, ≥90%