A versatile radical based approach to O-alkylated hydroxylamines and oximes

Béatrice Quiclet-Sire; Daniel Woollaston; Samir Z. Zard

doi:10.1016/j.tet.2008.08.113

A versatile radical based approach to O-alkylated hydroxylamines and oximes

Béatrice Quiclet-Sire
, Daniel Woollaston
, Samir Z. Zard

Laboratoire de Synthèse Organique

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

Abstract

O-Alkylhydroxylamines, often used for the preparation of bioconjugates, can be readily obtained by radical addition to suitable O-alkenylhydroxylamine derivatives. In the case of N-Boc-O-allylhydroxylamine, the addition is unexpectedly followed by elimination resulting in an overall allylation of the radical species.

Original language	English
Pages (from-to)	11917-11924
Number of pages	8
Journal	Tetrahedron
Volume	64
Issue number	52
DOIs	https://doi.org/10.1016/j.tet.2008.08.113
Publication status	Published - 22 Dec 2008
Externally published	Yes

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10.1016/j.tet.2008.08.113

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title = "A versatile radical based approach to O-alkylated hydroxylamines and oximes",

abstract = "O-Alkylhydroxylamines, often used for the preparation of bioconjugates, can be readily obtained by radical addition to suitable O-alkenylhydroxylamine derivatives. In the case of N-Boc-O-allylhydroxylamine, the addition is unexpectedly followed by elimination resulting in an overall allylation of the radical species.",

author = "B{\'e}atrice Quiclet-Sire and Daniel Woollaston and Zard, \{Samir Z.\}",

year = "2008",

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language = "English",

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T1 - A versatile radical based approach to O-alkylated hydroxylamines and oximes

AU - Quiclet-Sire, Béatrice

AU - Woollaston, Daniel

AU - Zard, Samir Z.

PY - 2008/12/22

Y1 - 2008/12/22

N2 - O-Alkylhydroxylamines, often used for the preparation of bioconjugates, can be readily obtained by radical addition to suitable O-alkenylhydroxylamine derivatives. In the case of N-Boc-O-allylhydroxylamine, the addition is unexpectedly followed by elimination resulting in an overall allylation of the radical species.

AB - O-Alkylhydroxylamines, often used for the preparation of bioconjugates, can be readily obtained by radical addition to suitable O-alkenylhydroxylamine derivatives. In the case of N-Boc-O-allylhydroxylamine, the addition is unexpectedly followed by elimination resulting in an overall allylation of the radical species.

U2 - 10.1016/j.tet.2008.08.113

DO - 10.1016/j.tet.2008.08.113

M3 - Article

AN - SCOPUS:56249143056

SN - 0040-4020

VL - 64

SP - 11917

EP - 11924

JO - Tetrahedron

JF - Tetrahedron

IS - 52

ER -

A versatile radical based approach to O-alkylated hydroxylamines and oximes

Abstract

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