Facile syntheses of 3-halo and mixed 3,5-dihalo analogues of N-acetyl-l-tyrosine via sulfonic acid-catalysed regioselective monohalogenation

Pakorn Bovonsombat; Pratheep Khanthapura; Michael M. Krause; Juthamard Leykajarakul

doi:10.1016/j.tetlet.2008.09.123

Facile syntheses of 3-halo and mixed 3,5-dihalo analogues of N-acetyl-l-tyrosine via sulfonic acid-catalysed regioselective monohalogenation

Pakorn Bovonsombat
, Pratheep Khanthapura
, Michael M. Krause
, Juthamard Leykajarakul

Science Division

Mahidol University

Research output: Contribution to journal › Article › peer-review

22 Citations (Scopus)

Abstract

The combination of catalytic amounts of p-toluenesulfonic acid and 1 equiv of N-halosuccinimide afforded highly selective ring-halogenation of N-acetyl-l-tyrosine, furnishing either N-acetyl-3-halo-l-tyrosine analogues or mixed 3,5-dihalo derivatives in a one-pot reaction with excellent yields at room temperature.

Original language	English
Pages (from-to)	7008-7011
Number of pages	4
Journal	Tetrahedron Letters
Volume	49
Issue number	49
DOIs	https://doi.org/10.1016/j.tetlet.2008.09.123
Publication status	Published - 1 Dec 2008

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10.1016/j.tetlet.2008.09.123

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title = "Facile syntheses of 3-halo and mixed 3,5-dihalo analogues of N-acetyl-l-tyrosine via sulfonic acid-catalysed regioselective monohalogenation",

abstract = "The combination of catalytic amounts of p-toluenesulfonic acid and 1 equiv of N-halosuccinimide afforded highly selective ring-halogenation of N-acetyl-l-tyrosine, furnishing either N-acetyl-3-halo-l-tyrosine analogues or mixed 3,5-dihalo derivatives in a one-pot reaction with excellent yields at room temperature.",

author = "Pakorn Bovonsombat and Pratheep Khanthapura and Krause, \{Michael M.\} and Juthamard Leykajarakul",

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language = "English",

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journal = "Tetrahedron Letters",

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T1 - Facile syntheses of 3-halo and mixed 3,5-dihalo analogues of N-acetyl-l-tyrosine via sulfonic acid-catalysed regioselective monohalogenation

AU - Bovonsombat, Pakorn

AU - Khanthapura, Pratheep

AU - Krause, Michael M.

AU - Leykajarakul, Juthamard

PY - 2008/12/1

Y1 - 2008/12/1

N2 - The combination of catalytic amounts of p-toluenesulfonic acid and 1 equiv of N-halosuccinimide afforded highly selective ring-halogenation of N-acetyl-l-tyrosine, furnishing either N-acetyl-3-halo-l-tyrosine analogues or mixed 3,5-dihalo derivatives in a one-pot reaction with excellent yields at room temperature.

AB - The combination of catalytic amounts of p-toluenesulfonic acid and 1 equiv of N-halosuccinimide afforded highly selective ring-halogenation of N-acetyl-l-tyrosine, furnishing either N-acetyl-3-halo-l-tyrosine analogues or mixed 3,5-dihalo derivatives in a one-pot reaction with excellent yields at room temperature.

UR - https://www.scopus.com/pages/publications/54049083330

U2 - 10.1016/j.tetlet.2008.09.123

DO - 10.1016/j.tetlet.2008.09.123

M3 - Article

AN - SCOPUS:54049083330

SN - 0040-4039

VL - 49

SP - 7008

EP - 7011

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 49

ER -

Facile syntheses of 3-halo and mixed 3,5-dihalo analogues of N-acetyl-l-tyrosine via sulfonic acid-catalysed regioselective monohalogenation

Abstract

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