Synthesis of azepine derivatives by rhodium-catalyzed tandem 2,3-rearrangement/heterocyclization

Itaru Nakamura; Masashi Okamoto; Yoshinori Sato; Masahiro Terada

doi:10.1002/anie.201205285

Synthesis of azepine derivatives by rhodium-catalyzed tandem 2,3-rearrangement/heterocyclization

Itaru Nakamura, Masashi Okamoto, Yoshinori Sato, Masahiro Terada

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

63 Citations (Scopus)

Abstract

Easy to N-cycle: The efficient synthesis of azepine derivatives was achieved by Rh-catalyzed tandem 2,3-rearrangement involving the heterocyclization of N-allenylnitrone intermediates (see scheme; cod=1,5-cyclooctadiene, tppms=sodium diphenylphosphinobenzene-3-sulfonate).

Original language	English
Pages (from-to)	10816-10819
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	43
DOIs	https://doi.org/10.1002/anie.201205285
Publication status	Published - 2012 Oct 22

Keywords

alkynes
nitrogen heterocycles
rearrangement
rhodium
ring expansion

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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abstract = "Easy to N-cycle: The efficient synthesis of azepine derivatives was achieved by Rh-catalyzed tandem 2,3-rearrangement involving the heterocyclization of N-allenylnitrone intermediates (see scheme; cod=1,5-cyclooctadiene, tppms=sodium diphenylphosphinobenzene-3-sulfonate).",

keywords = "alkynes, nitrogen heterocycles, rearrangement, rhodium, ring expansion",

author = "Itaru Nakamura and Masashi Okamoto and Yoshinori Sato and Masahiro Terada",

year = "2012",

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volume = "51",

pages = "10816--10819",

journal = "Angewandte Chemie - International Edition",

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T1 - Synthesis of azepine derivatives by rhodium-catalyzed tandem 2,3-rearrangement/heterocyclization

AU - Nakamura, Itaru

AU - Okamoto, Masashi

AU - Sato, Yoshinori

AU - Terada, Masahiro

PY - 2012/10/22

Y1 - 2012/10/22

N2 - Easy to N-cycle: The efficient synthesis of azepine derivatives was achieved by Rh-catalyzed tandem 2,3-rearrangement involving the heterocyclization of N-allenylnitrone intermediates (see scheme; cod=1,5-cyclooctadiene, tppms=sodium diphenylphosphinobenzene-3-sulfonate).

AB - Easy to N-cycle: The efficient synthesis of azepine derivatives was achieved by Rh-catalyzed tandem 2,3-rearrangement involving the heterocyclization of N-allenylnitrone intermediates (see scheme; cod=1,5-cyclooctadiene, tppms=sodium diphenylphosphinobenzene-3-sulfonate).

KW - alkynes

KW - nitrogen heterocycles

KW - rearrangement

KW - rhodium

KW - ring expansion

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