Synthesis of α,β,γ,δ-unsaturated imines from N-Sulfonyl-1,2,3-triazoles and allenes through rhodium-catalyzed cyclopropanation and thermal rearrangement

Tomoya Miura; Takayuki Nakamuro; Tsuneaki Biyajima; Masahiro Murakami

doi:10.1246/cl.150080

Synthesis of α,β,γ,δ-unsaturated imines from N-Sulfonyl-1,2,3-triazoles and allenes through rhodium-catalyzed cyclopropanation and thermal rearrangement

Tomoya Miura, Takayuki Nakamuro, Tsuneaki Biyajima, Masahiro Murakami

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

15 Citations (Scopus)

Abstract

α,β,γ,δ-Unsaturated imines are synthesized from N-sulfonyl-1,2,3-triazoles and allenes. Allenes are initially cyclopropanated by intermediate α-imino rhodium carbene complexes, and the resulting alkylidenecyclopropyl methanimines undergo a ringopening thermal rearrangement to afford the corresponding α,β,γ,δ-unsaturated imines.

Original language	English
Pages (from-to)	700-702
Number of pages	3
Journal	Chemistry Letters
Volume	44
Issue number	5
DOIs	https://doi.org/10.1246/cl.150080
Publication status	Published - 2015
Externally published	Yes

ASJC Scopus subject areas

Chemistry(all)

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title = "Synthesis of α,β,γ,δ-unsaturated imines from N-Sulfonyl-1,2,3-triazoles and allenes through rhodium-catalyzed cyclopropanation and thermal rearrangement",

abstract = "α,β,γ,δ-Unsaturated imines are synthesized from N-sulfonyl-1,2,3-triazoles and allenes. Allenes are initially cyclopropanated by intermediate α-imino rhodium carbene complexes, and the resulting alkylidenecyclopropyl methanimines undergo a ringopening thermal rearrangement to afford the corresponding α,β,γ,δ-unsaturated imines.",

author = "Tomoya Miura and Takayuki Nakamuro and Tsuneaki Biyajima and Masahiro Murakami",

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language = "English",

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pages = "700--702",

journal = "Chemistry Letters",

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T1 - Synthesis of α,β,γ,δ-unsaturated imines from N-Sulfonyl-1,2,3-triazoles and allenes through rhodium-catalyzed cyclopropanation and thermal rearrangement

AU - Miura, Tomoya

AU - Nakamuro, Takayuki

AU - Biyajima, Tsuneaki

AU - Murakami, Masahiro

PY - 2015

Y1 - 2015

N2 - α,β,γ,δ-Unsaturated imines are synthesized from N-sulfonyl-1,2,3-triazoles and allenes. Allenes are initially cyclopropanated by intermediate α-imino rhodium carbene complexes, and the resulting alkylidenecyclopropyl methanimines undergo a ringopening thermal rearrangement to afford the corresponding α,β,γ,δ-unsaturated imines.

AB - α,β,γ,δ-Unsaturated imines are synthesized from N-sulfonyl-1,2,3-triazoles and allenes. Allenes are initially cyclopropanated by intermediate α-imino rhodium carbene complexes, and the resulting alkylidenecyclopropyl methanimines undergo a ringopening thermal rearrangement to afford the corresponding α,β,γ,δ-unsaturated imines.

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ER -

Synthesis of α,β,γ,δ-unsaturated imines from N-Sulfonyl-1,2,3-triazoles and allenes through rhodium-catalyzed cyclopropanation and thermal rearrangement

Abstract

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