NovelN-transfer reagent for converting α-amino acid derivatives to α-diazo compounds

Guan Han Lu; Tzu Chia Huang; Hsiao Chin Hsueh; Shin Cherng Yang; Ting Wei Cho; Ho Hsuan Chou

doi:10.1039/d1cc01285a

NovelN-transfer reagent for converting α-amino acid derivatives to α-diazo compounds

Guan Han Lu, Tzu Chia Huang, Hsiao Chin Hsueh, Shin Cherng Yang, Ting Wei Cho, Ho Hsuan Chou

Department of Chemistry

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

7 Citations (Scopus)

Abstract

A novel universalN-transfer reagent for direct and effective transformation of α-amino ketones, acetamides, and esters to the corresponding α-diazo products under mild basic conditions has been developed. This one-step synthetic approach not only allows for generation of α-substituted-α-diazo carbonyl compounds from α-amino acid derivatives but also permits preparation of α-diazo dipeptides fromN-terminal dipeptides (32 examples, up to 91%).

Original language	English
Pages (from-to)	4839-4842
Number of pages	4
Journal	Chemical Communications
Volume	57
Issue number	39
DOIs	https://doi.org/10.1039/d1cc01285a
Publication status	Published - 2021 May 14

All Science Journal Classification (ASJC) codes

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/d1cc01285a

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title = "NovelN-transfer reagent for converting α-amino acid derivatives to α-diazo compounds",

abstract = "A novel universalN-transfer reagent for direct and effective transformation of α-amino ketones, acetamides, and esters to the corresponding α-diazo products under mild basic conditions has been developed. This one-step synthetic approach not only allows for generation of α-substituted-α-diazo carbonyl compounds from α-amino acid derivatives but also permits preparation of α-diazo dipeptides fromN-terminal dipeptides (32 examples, up to 91%).",

author = "Lu, {Guan Han} and Huang, {Tzu Chia} and Hsueh, {Hsiao Chin} and Yang, {Shin Cherng} and Cho, {Ting Wei} and Chou, {Ho Hsuan}",

note = "Funding Information: This work was funded by the Ministry of Science and Technology of Taiwan (MOST 105-2113-M-006-012-MY2). The 500 MHz NMR, HRMS, CE/LC–MS at the Instrumentation Center at National Cheng Kung University are acknowledged. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2021.",

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doi = "10.1039/d1cc01285a",

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T1 - NovelN-transfer reagent for converting α-amino acid derivatives to α-diazo compounds

AU - Lu, Guan Han

AU - Huang, Tzu Chia

AU - Hsueh, Hsiao Chin

AU - Yang, Shin Cherng

AU - Cho, Ting Wei

AU - Chou, Ho Hsuan

N1 - Funding Information: This work was funded by the Ministry of Science and Technology of Taiwan (MOST 105-2113-M-006-012-MY2). The 500 MHz NMR, HRMS, CE/LC–MS at the Instrumentation Center at National Cheng Kung University are acknowledged. Publisher Copyright: © The Royal Society of Chemistry 2021.

PY - 2021/5/14

Y1 - 2021/5/14

N2 - A novel universalN-transfer reagent for direct and effective transformation of α-amino ketones, acetamides, and esters to the corresponding α-diazo products under mild basic conditions has been developed. This one-step synthetic approach not only allows for generation of α-substituted-α-diazo carbonyl compounds from α-amino acid derivatives but also permits preparation of α-diazo dipeptides fromN-terminal dipeptides (32 examples, up to 91%).

AB - A novel universalN-transfer reagent for direct and effective transformation of α-amino ketones, acetamides, and esters to the corresponding α-diazo products under mild basic conditions has been developed. This one-step synthetic approach not only allows for generation of α-substituted-α-diazo carbonyl compounds from α-amino acid derivatives but also permits preparation of α-diazo dipeptides fromN-terminal dipeptides (32 examples, up to 91%).

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NovelN-transfer reagent for converting α-amino acid derivatives to α-diazo compounds

Abstract

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