Literature DB >> 20361802

Sulfonylation-induced N- to O-acetyl migration in 2-acetamidoethanol derivatives.

Takao Yamaguchi1, Dusan Hesek, Mijoon Lee, Allen G Oliver, Shahriar Mobashery.   

Abstract

The first example of sulfonylation-induced N- to O-acetyl migration of 2-acetamidoethanol derivatives is described. This type of reaction could happen with any 2-acetamidoethanol derivatives under typical sulfonylation conditions (TsCl or MsCl, pyridine) and might be a common side reaction of significance. Furthermore, the results reveal that 2-acetamidoethanol derivatives with a sterically encumbered hydroxyl group result in the migration products in high yields. The mechanism of the migration reaction is discussed.

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Year:  2010        PMID： 20361802      PMCID： PMC2878608          DOI： 10.1021/jo100456z

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  10 in total

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Journal:  J Org Chem       Date:  2008-08-09       Impact factor: 4.354

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Journal:  Org Biomol Chem       Date:  2003-05-07       Impact factor: 3.876

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  10 in total
  2 in total

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2.  Inhibitors for Bacterial Cell-Wall Recycling.

Authors:  Takao Yamaguchi; Blas Blázquez; Dusan Hesek; Mijoon Lee; Leticia I Llarrull; Bill Boggess; Allen G Oliver; Jed F Fisher; Shahriar Mobashery
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  2 in total

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