Iron-catalyzed α-amidation of heterocycles with potential route to amino alcohols, amino thiols, and diamino products by nucleophilic ring opening.

Iron-catalyzed α-amidation of heterocycles with potential route to amino alcohols, amino thiols, and diamino products by nucleophilic ring opening.

An efficient method for α-amidation of heterocyclic moieties via direct nitrene insertion catalyzed by iron(III)trifluoromethanesulfonate with PhI=NTs (Ts = p-toluenesulfonyl)as a nitrogen source is reported herein. This reaction was shown to be applicable to cyclic ethers, cyclic thioethers, and py...

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Main Author: Tania, Stefani.
Other Authors: Philip Wai Hong Chan
Format: Final Year Project
Language:English
Published: 2010
Subjects:
DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis
Online Access:http://hdl.handle.net/10356/39888
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-398882023-02-28T23:12:32Z Iron-catalyzed α-amidation of heterocycles with potential route to amino alcohols, amino thiols, and diamino products by nucleophilic ring opening. Tania, Stefani. Philip Wai Hong Chan School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis An efficient method for α-amidation of heterocyclic moieties via direct nitrene insertion catalyzed by iron(III)trifluoromethanesulfonate with PhI=NTs (Ts = p-toluenesulfonyl)as a nitrogen source is reported herein. This reaction was shown to be applicable to cyclic ethers, cyclic thioethers, and pyrrolidines to afford the α-amino products in moderate to excellent yields. These amidated compounds were also shown to readily undergo nucleophilic ring opening to give amino alcohols, amino thiols, and diamino products in moderate to excellent yields. Bachelor of Science in Chemistry and Biological Chemistry 2010-06-07T08:58:42Z 2010-06-07T08:58:42Z 2010 2010 Final Year Project (FYP) http://hdl.handle.net/10356/39888 en 28 p. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis
spellingShingle DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis
Tania, Stefani.
Iron-catalyzed α-amidation of heterocycles with potential route to amino alcohols, amino thiols, and diamino products by nucleophilic ring opening.
description An efficient method for α-amidation of heterocyclic moieties via direct nitrene insertion catalyzed by iron(III)trifluoromethanesulfonate with PhI=NTs (Ts = p-toluenesulfonyl)as a nitrogen source is reported herein. This reaction was shown to be applicable to cyclic ethers, cyclic thioethers, and pyrrolidines to afford the α-amino products in moderate to excellent yields. These amidated compounds were also shown to readily undergo nucleophilic ring opening to give amino alcohols, amino thiols, and diamino products in moderate to excellent yields.
author2 Philip Wai Hong Chan
author_facet Philip Wai Hong Chan
Tania, Stefani.
format Final Year Project
author Tania, Stefani.
author_sort Tania, Stefani.
title Iron-catalyzed α-amidation of heterocycles with potential route to amino alcohols, amino thiols, and diamino products by nucleophilic ring opening.
title_short Iron-catalyzed α-amidation of heterocycles with potential route to amino alcohols, amino thiols, and diamino products by nucleophilic ring opening.
title_full Iron-catalyzed α-amidation of heterocycles with potential route to amino alcohols, amino thiols, and diamino products by nucleophilic ring opening.
title_fullStr Iron-catalyzed α-amidation of heterocycles with potential route to amino alcohols, amino thiols, and diamino products by nucleophilic ring opening.
title_full_unstemmed Iron-catalyzed α-amidation of heterocycles with potential route to amino alcohols, amino thiols, and diamino products by nucleophilic ring opening.
title_sort iron-catalyzed α-amidation of heterocycles with potential route to amino alcohols, amino thiols, and diamino products by nucleophilic ring opening.
publishDate 2010
url http://hdl.handle.net/10356/39888
_version_ 1759853920263340032

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