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Synlett 2018; 29(15): 2015-2018
DOI: 10.1055/s-0037-1610262
letter
© Georg Thieme Verlag Stuttgart · New York

The Acceleration of the Rearrangement of α-Hydroxy Aldimines by Lewis or Brønsted Acids

Xin Zhang
,
Yijing Dai
,
William D. Wulff*
Department of Chemistry, Michigan State University, East Lansing, MI 48824, USA   Email: wulff@chemistry.msu.edu
› Author AffiliationsThis work was supported by a grant from the National Institute of General Medical Sciences (GM094478).
Further Information

Publication History

Received: 03 August 2018

Accepted after revision: 05 August 2018

Publication Date:
28 August 2018 (online)

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Abstract

An efficient method was developed for the synthesis of α-amino ketones from α-hydroxy imines. The reaction occurs through an α-iminol rearrangement involving the migration of a substituent of the carbinol carbon to the imine carbon. The optimal catalysts were found to be silica gel or montmorillonite K 10, which effected migration of a variety of aryl and alkyl substituents in high yields. The rearrangement can also be carried out on imines generated in situ from aldehydes and amines in essentially the same yields as those from the preformed imines.

Key words

iminol rearrangement - silica gel - montmorillonite - catalysis - amino ketone - hydroxy imines
 

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