Allylic C-H amination for the preparation of syn-1,3-amino alcohol motifs

Grant T. Rice; M. Christina White

doi:10.1021/ja9054959

Allylic C-H amination for the preparation of syn-1,3-amino alcohol motifs

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

Abstract

A highly selective and general Pd/sulfoxide-catalyzed allylic C-H amination reaction en route to syn-1,3-amino alcohol motifs is reported. Key to achieving this reactivity under mild conditions is the use of electron-deficient N-nosyl carbamate nucleophiles that are thought to promote functionalization by furnishing higher concentrations of anionic species in situ. The reaction is shown to be orthogonal to classical C-C bond-forming/-reduction sequences as well as nitrene-based C-H amination methods.

Original language	English (US)
Pages (from-to)	11707-11711
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	131
Issue number	33
DOIs	https://doi.org/10.1021/ja9054959
State	Published - Aug 26 2009

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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title = "Allylic C-H amination for the preparation of syn-1,3-amino alcohol motifs",

abstract = "A highly selective and general Pd/sulfoxide-catalyzed allylic C-H amination reaction en route to syn-1,3-amino alcohol motifs is reported. Key to achieving this reactivity under mild conditions is the use of electron-deficient N-nosyl carbamate nucleophiles that are thought to promote functionalization by furnishing higher concentrations of anionic species in situ. The reaction is shown to be orthogonal to classical C-C bond-forming/-reduction sequences as well as nitrene-based C-H amination methods.",

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