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

School of Molecular Sciences

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
Article number	e1600320
Number of pages	8
Journal	Helvetica Chimica Acta
Volume	100
Issue number	2
DOIs	https://doi.org/10.1002/hlca.201600320
Publication status	Published - Feb 2017

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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",

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doi = "10.1002/hlca.201600320",

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T1 - Synthesis of 2-Substituted 2-Amino Ketones by Rhodium-Catalyzed Reaction of N-Sulfonyl-1,2,3-triazoles with 2-Alkenols

AU - Miura, Tomoya

AU - Tanaka, Takamasa

AU - Zhao, Qiang

AU - Stewart, Scott G.

AU - Murakami, Masahiro

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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DO - 10.1002/hlca.201600320

M3 - Article

SN - 0018-019X

VL - 100

JO - Helvetica Chimica Acta

JF - Helvetica Chimica Acta

IS - 2

M1 - e1600320

ER -

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

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