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A Facile Highly Regio- and Stereoselective Preparation of N-Tosyl Allylic Amines from Allylic Alcohols and Tosyl Isocyanate via Palladium(II)-Catalyzed Aminopalladation-β-Heteroatom Elimination

Aiwen Lei and Xiyan Lu*

*Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, 200032, China, Email:

A. Lei, X. Lu, Org. Lett., 2000, 2, 2357-2360.

DOI: 10.1021/ol006130u


A one-pot reaction of allylic alcohols with tosyl isocyanate followed by palladium(II)-catalyzed allylic substitution gives N-tosyl (E)-allylic amines in high yield. The allylic substitution reaction occurs with high regio- and stereoselectivity only at the γ-position of the 1- or 3-substituted allylic alcohols.

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proposed mechanism

Key Words

allylic amines, sulfonamides

ID: J54-Y2000