Synthesis of 2-Substituted 2-Amino Ketones by Rhodium-Catalyzed Reaction of N-Sulfonyl-1,2,3-triazoles with 2-Alkenols

Tomoya Miura; Takamasa Tanaka; Qiang Zhao; Scott G. Stewart; Masahiro Murakami

doi:10.1002/hlca.201600320

Synthesis of 2-Substituted 2-Amino Ketones by Rhodium-Catalyzed Reaction of N-Sulfonyl-1,2,3-triazoles with 2-Alkenols

Tomoya Miura, Takamasa Tanaka, Qiang Zhao, Scott G. Stewart, Masahiro Murakami

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

16 Citations (Scopus)

Abstract

A study on a rhodium(II)-catalyzed reaction of N-sulfonyl-1,2,3-triazoles with 2-alkenols is reported. The reaction is initiated by insertion of an α-imino carbene into the O–H linkage of alcohol, forming a 2-alkenoxy enamide intermediate. A thermal [3,3]-sigmatropic rearrangement follows to yield 2-substituted 2-amino ketone in a stereoselective manner. The successful application of this methodology to a formal synthesis of (–)-α-conhydrine is also described.

Original language	English
Journal	Helvetica Chimica Acta
Volume	100
Issue number	2
DOIs	https://doi.org/10.1002/hlca.201600320
Publication status	Published - Feb 2017
Externally published	Yes

Keywords

2-Amino ketones
Carbenoids
Rhodium
Sigmatropic rearrangements
Triazoles

ASJC Scopus subject areas

Catalysis
Biochemistry
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1002/hlca.201600320

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title = "Synthesis of 2-Substituted 2-Amino Ketones by Rhodium-Catalyzed Reaction of N-Sulfonyl-1,2,3-triazoles with 2-Alkenols",

abstract = "A study on a rhodium(II)-catalyzed reaction of N-sulfonyl-1,2,3-triazoles with 2-alkenols is reported. The reaction is initiated by insertion of an α-imino carbene into the O–H linkage of alcohol, forming a 2-alkenoxy enamide intermediate. A thermal [3,3]-sigmatropic rearrangement follows to yield 2-substituted 2-amino ketone in a stereoselective manner. The successful application of this methodology to a formal synthesis of (–)-α-conhydrine is also described.",

keywords = "2-Amino ketones, Carbenoids, Rhodium, Sigmatropic rearrangements, Triazoles",

author = "Tomoya Miura and Takamasa Tanaka and Qiang Zhao and Stewart, {Scott G.} and Masahiro Murakami",

note = "Funding Information: This work was supported in part by Grants-in-Aid for Scientific Research (S) (15H05756) and (C) (16K05694) from MEXT. Q.Z. acknowledged JSPS fellowship for young scientists. S.G.S. is grateful for the JSPS invitation fellowship for research in Japan. Publisher Copyright: {\textcopyright} 2017 Wiley-VHCA AG, Zurich, Switzerland",

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month = feb,

doi = "10.1002/hlca.201600320",

language = "English",

volume = "100",

journal = "Helvetica Chimica Acta",

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AU - Miura, Tomoya

AU - Tanaka, Takamasa

AU - Zhao, Qiang

AU - Stewart, Scott G.

AU - Murakami, Masahiro

N1 - Funding Information: This work was supported in part by Grants-in-Aid for Scientific Research (S) (15H05756) and (C) (16K05694) from MEXT. Q.Z. acknowledged JSPS fellowship for young scientists. S.G.S. is grateful for the JSPS invitation fellowship for research in Japan. Publisher Copyright: © 2017 Wiley-VHCA AG, Zurich, Switzerland

PY - 2017/2

Y1 - 2017/2

N2 - A study on a rhodium(II)-catalyzed reaction of N-sulfonyl-1,2,3-triazoles with 2-alkenols is reported. The reaction is initiated by insertion of an α-imino carbene into the O–H linkage of alcohol, forming a 2-alkenoxy enamide intermediate. A thermal [3,3]-sigmatropic rearrangement follows to yield 2-substituted 2-amino ketone in a stereoselective manner. The successful application of this methodology to a formal synthesis of (–)-α-conhydrine is also described.

AB - A study on a rhodium(II)-catalyzed reaction of N-sulfonyl-1,2,3-triazoles with 2-alkenols is reported. The reaction is initiated by insertion of an α-imino carbene into the O–H linkage of alcohol, forming a 2-alkenoxy enamide intermediate. A thermal [3,3]-sigmatropic rearrangement follows to yield 2-substituted 2-amino ketone in a stereoselective manner. The successful application of this methodology to a formal synthesis of (–)-α-conhydrine is also described.

KW - 2-Amino ketones

KW - Carbenoids

KW - Rhodium

KW - Sigmatropic rearrangements

KW - Triazoles

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Synthesis of 2-Substituted 2-Amino Ketones by Rhodium-Catalyzed Reaction of N-Sulfonyl-1,2,3-triazoles with 2-Alkenols

Abstract

Keywords

ASJC Scopus subject areas

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