Oxazepine synthesis by copper-catalyzed intermolecular cascade reactions between O-propargylic oximes and dipolarophiles

Itaru Nakamura; Yu Kudo; Masahiro Terada

doi:10.1002/anie.201302751

Oxazepine synthesis by copper-catalyzed intermolecular cascade reactions between O-propargylic oximes and dipolarophiles

Itaru Nakamura, Yu Kudo, Masahiro Terada

Tohoku University

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

41 Citations (Scopus)

Abstract

Three-step cascade: Oxazepine derivatives were efficiently prepared from O-propargylic oximes and dipolarophiles through copper-catalyzed cascade reactions which proceed through a 2,3-rearrangement, [3+2] cycloaddition, and subsequent 1,3-oxygen rearrangement. The process involves the cleavage of C-O and N-O bonds.

Original language	English
Pages (from-to)	7536-7539
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	29
DOIs	https://doi.org/10.1002/anie.201302751
Publication status	Published - 2013 Jul 15

Keywords

copper
cycloaddition
heterocycles
rearrangement
synthetic methods

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10.1002/anie.201302751

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abstract = "Three-step cascade: Oxazepine derivatives were efficiently prepared from O-propargylic oximes and dipolarophiles through copper-catalyzed cascade reactions which proceed through a 2,3-rearrangement, [3+2] cycloaddition, and subsequent 1,3-oxygen rearrangement. The process involves the cleavage of C-O and N-O bonds.",

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AU - Kudo, Yu

AU - Terada, Masahiro

PY - 2013/7/15

Y1 - 2013/7/15

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AB - Three-step cascade: Oxazepine derivatives were efficiently prepared from O-propargylic oximes and dipolarophiles through copper-catalyzed cascade reactions which proceed through a 2,3-rearrangement, [3+2] cycloaddition, and subsequent 1,3-oxygen rearrangement. The process involves the cleavage of C-O and N-O bonds.

KW - copper

KW - cycloaddition

KW - heterocycles

KW - rearrangement

KW - synthetic methods

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Oxazepine synthesis by copper-catalyzed intermolecular cascade reactions between O-propargylic oximes and dipolarophiles

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Keywords

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