Silicon-Directed Rhenium-Catalyzed Allylic Substitutions with N‑Hydroxycarbamates, N‑Hydroxysulfonamides, and Hydroxamic Acids

Sanjay W. Chavhan; Catherine A. McAdam; Matthew J. Cook

doi:10.1021/jo501992p

Silicon-Directed Rhenium-Catalyzed Allylic Substitutions with N‑Hydroxycarbamates, N‑Hydroxysulfonamides, and Hydroxamic Acids

Sanjay W. Chavhan, Catherine A. McAdam, Matthew J. Cook

School of Chemistry and Chemical Engineering

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

13 Citations (Scopus)

Abstract

A rhenium-catalyzed N-selective allylic amination reaction of N-hydroxycarbamates has been developed. This reaction occurs with excellent N/O selectivity and with complete carbon selectivity on the allylic system. The reaction is tolerant of many functional groups and also proceeds with N-hydroxysulfonamides and hydroxamic acids.

Original language	English
Pages (from-to)	11234−11240
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	79
Issue number	22
Early online date	03 Nov 2014
DOIs	https://doi.org/10.1021/jo501992p
Publication status	Published - 2014

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title = "Silicon-Directed Rhenium-Catalyzed Allylic Substitutions with N‑Hydroxycarbamates, N‑Hydroxysulfonamides, and Hydroxamic Acids",

abstract = "A rhenium-catalyzed N-selective allylic amination reaction of N-hydroxycarbamates has been developed. This reaction occurs with excellent N/O selectivity and with complete carbon selectivity on the allylic system. The reaction is tolerant of many functional groups and also proceeds with N-hydroxysulfonamides and hydroxamic acids.",

author = "Chavhan, {Sanjay W.} and McAdam, {Catherine A.} and Cook, {Matthew J.}",

year = "2014",

doi = "10.1021/jo501992p",

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journal = "Journal of Organic Chemistry",

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T1 - Silicon-Directed Rhenium-Catalyzed Allylic Substitutions with N‑Hydroxycarbamates, N‑Hydroxysulfonamides, and Hydroxamic Acids

AU - Chavhan, Sanjay W.

AU - McAdam, Catherine A.

AU - Cook, Matthew J.

PY - 2014

Y1 - 2014

N2 - A rhenium-catalyzed N-selective allylic amination reaction of N-hydroxycarbamates has been developed. This reaction occurs with excellent N/O selectivity and with complete carbon selectivity on the allylic system. The reaction is tolerant of many functional groups and also proceeds with N-hydroxysulfonamides and hydroxamic acids.

AB - A rhenium-catalyzed N-selective allylic amination reaction of N-hydroxycarbamates has been developed. This reaction occurs with excellent N/O selectivity and with complete carbon selectivity on the allylic system. The reaction is tolerant of many functional groups and also proceeds with N-hydroxysulfonamides and hydroxamic acids.

U2 - 10.1021/jo501992p

DO - 10.1021/jo501992p

M3 - Article

SN - 0022-3263

VL - 79

SP - 11234−11240

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 22

ER -

Silicon-Directed Rhenium-Catalyzed Allylic Substitutions with N‑Hydroxycarbamates, N‑Hydroxysulfonamides, and Hydroxamic Acids

Abstract

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