3-Methylene-4-amido-1,2-diazetidine as a Formal 1,4-Dipole Precursor: Lewis Acid-Catalyzed Nucleophilic Addition with Silylated Nucleophiles

Takashi Okitsu; Keiko Kobayashi; Ryosuke Kan; Yuji Yoshida; Yuki Matsui; Akimori Wada

doi:10.1021/acs.orglett.7b02194

3-Methylene-4-amido-1,2-diazetidine as a Formal 1,4-Dipole Precursor: Lewis Acid-Catalyzed Nucleophilic Addition with Silylated Nucleophiles

Takashi Okitsu^*, Keiko Kobayashi, Ryosuke Kan, Yuji Yoshida, Yuki Matsui, Akimori Wada

^*Corresponding author for this work

Synthetic and Biomolecular Organic Chemistry

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

14 Scopus citations

Abstract

3-Methylene-4-amido-1,2-diazetidine (MADA) was prepared for the first time via formal [2 + 2] cycloaddition of an allenamide and an azodicarboxylate. MADA worked as a formal 1,4-dipole precursor toward nucleophilic addition with various silyl enol ethers and allyltrimethylsilanes.

Original language	English
Pages (from-to)	4592-4595
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	17
DOIs	https://doi.org/10.1021/acs.orglett.7b02194
State	Published - 2017/09/01

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "3-Methylene-4-amido-1,2-diazetidine as a Formal 1,4-Dipole Precursor: Lewis Acid-Catalyzed Nucleophilic Addition with Silylated Nucleophiles",

abstract = "3-Methylene-4-amido-1,2-diazetidine (MADA) was prepared for the first time via formal [2 + 2] cycloaddition of an allenamide and an azodicarboxylate. MADA worked as a formal 1,4-dipole precursor toward nucleophilic addition with various silyl enol ethers and allyltrimethylsilanes.",

author = "Takashi Okitsu and Keiko Kobayashi and Ryosuke Kan and Yuji Yoshida and Yuki Matsui and Akimori Wada",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

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doi = "10.1021/acs.orglett.7b02194",

language = "英語",

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T1 - 3-Methylene-4-amido-1,2-diazetidine as a Formal 1,4-Dipole Precursor

T2 - Lewis Acid-Catalyzed Nucleophilic Addition with Silylated Nucleophiles

AU - Okitsu, Takashi

AU - Kobayashi, Keiko

AU - Kan, Ryosuke

AU - Yoshida, Yuji

AU - Matsui, Yuki

AU - Wada, Akimori

PY - 2017/9/1

Y1 - 2017/9/1

N2 - 3-Methylene-4-amido-1,2-diazetidine (MADA) was prepared for the first time via formal [2 + 2] cycloaddition of an allenamide and an azodicarboxylate. MADA worked as a formal 1,4-dipole precursor toward nucleophilic addition with various silyl enol ethers and allyltrimethylsilanes.

AB - 3-Methylene-4-amido-1,2-diazetidine (MADA) was prepared for the first time via formal [2 + 2] cycloaddition of an allenamide and an azodicarboxylate. MADA worked as a formal 1,4-dipole precursor toward nucleophilic addition with various silyl enol ethers and allyltrimethylsilanes.

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DO - 10.1021/acs.orglett.7b02194

M3 - 学術論文

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AN - SCOPUS:85028767938

SN - 1523-7060

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JO - Organic Letters

JF - Organic Letters

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ER -

3-Methylene-4-amido-1,2-diazetidine as a Formal 1,4-Dipole Precursor: Lewis Acid-Catalyzed Nucleophilic Addition with Silylated Nucleophiles

Abstract

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