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

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.

SUBMITTER: Yamaguchi T

PROVIDER: S-EPMC2878608 | biostudies-literature | 2010 May

REPOSITORIES: biostudies-literature

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

Yamaguchi Takao T Hesek Dusan D Lee Mijoon M Oliver Allen G AG Mobashery Shahriar S

The Journal of organic chemistry 20100501 10

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 ...[more]

PMID: 20361802

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