Rapid Access to Nitrogenous Heterobicycles via RhIII-Catalyzed Isomerization from Alkynes to Allenes

Itaru Nakamura; Keisuke Takeda; Yoshinori Sato; Masahiro Terada

doi:10.1002/chem.201701704

Rapid Access to Nitrogenous Heterobicycles via Rh^III-Catalyzed Isomerization from Alkynes to Allenes

Itaru Nakamura, Keisuke Takeda, Yoshinori Sato, Masahiro Terada

Tohoku University

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

2 Citations (Scopus)

Abstract

We show that N-alkynylnitrones are efficiently converted to nitrogenous heterobicyclic compounds with a nitrogen atom at the bridgehead position by using a Rh^III-catalyst. Our mechanistic studies suggest that the reaction proceeds via an allene intermediate, which is generated in situ through Rh^III-catalyzed isomerization of the alkyne group.

Original language	English
Pages (from-to)	7686-7688
Number of pages	3
Journal	Chemistry - A European Journal
Volume	23
Issue number	32
DOIs	https://doi.org/10.1002/chem.201701704
Publication status	Published - 2017 Jun 7

Keywords

allenes
cascade reaction
heterocycles
rearrangement
rhodium

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10.1002/chem.201701704

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title = "Rapid Access to Nitrogenous Heterobicycles via RhIII-Catalyzed Isomerization from Alkynes to Allenes",

abstract = "We show that N-alkynylnitrones are efficiently converted to nitrogenous heterobicyclic compounds with a nitrogen atom at the bridgehead position by using a RhIII-catalyst. Our mechanistic studies suggest that the reaction proceeds via an allene intermediate, which is generated in situ through RhIII-catalyzed isomerization of the alkyne group.",

keywords = "allenes, cascade reaction, heterocycles, rearrangement, rhodium",

author = "Itaru Nakamura and Keisuke Takeda and Yoshinori Sato and Masahiro Terada",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Number JP16H00996 in Precisely Designed Catalysts with Customized Scaffolding. Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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AU - Nakamura, Itaru

AU - Takeda, Keisuke

AU - Sato, Yoshinori

AU - Terada, Masahiro

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant Number JP16H00996 in Precisely Designed Catalysts with Customized Scaffolding. Publisher Copyright: © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2017/6/7

Y1 - 2017/6/7

N2 - We show that N-alkynylnitrones are efficiently converted to nitrogenous heterobicyclic compounds with a nitrogen atom at the bridgehead position by using a RhIII-catalyst. Our mechanistic studies suggest that the reaction proceeds via an allene intermediate, which is generated in situ through RhIII-catalyzed isomerization of the alkyne group.

AB - We show that N-alkynylnitrones are efficiently converted to nitrogenous heterobicyclic compounds with a nitrogen atom at the bridgehead position by using a RhIII-catalyst. Our mechanistic studies suggest that the reaction proceeds via an allene intermediate, which is generated in situ through RhIII-catalyzed isomerization of the alkyne group.

KW - allenes

KW - cascade reaction

KW - heterocycles

KW - rearrangement

KW - rhodium

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JF - Chemistry - A European Journal

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ER -

Rapid Access to Nitrogenous Heterobicycles via Rh^III-Catalyzed Isomerization from Alkynes to Allenes

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