Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/154825
Title: Iterative addition of carbon nucleophiles toN,N-dialkyl carboxamides for synthesis of α-tertiary amines
Authors: Chen, Jiahua
Lim, Jun Wei
Ong, Derek Yiren
Chiba, Shunsuke
Keywords: Science::Chemistry
Issue Date: 2022
Source: Chen, J., Lim, J. W., Ong, D. Y. & Chiba, S. (2022). Iterative addition of carbon nucleophiles toN,N-dialkyl carboxamides for synthesis of α-tertiary amines. Chemical Science, 13(1), 99-104. https://dx.doi.org/10.1039/d1sc05876b
Project: MOE2019-T2-1-089
Journal: Chemical Science
Abstract: A protocol for the synthesis of α-tertiary amines was developed by iterative addition of carbon nucleophiles toN,N-dialkyl carboxamides. Nucleophilic 1,2-addition of organolithium reagents to carboxamides forms anionic tetrahedral carbinolamine (hemiaminal) intermediates, which are subsequently treated with bromotrimethylsilane (Me3SiBr) followed by organomagnesium (Grignard) reagents, organolithium reagents or tetrabutylammonium cyanide, affording α-tertiary amines. Employment of (trimethylsilyl)methylmagnesium bromide as the 2ndnucleophile allowed for aza-Peterson olefination of the resulting α-tertiary (trimethylsilyl)methylamines with acidic work-up, resulting in the formation of 1,1-diarylethylenes.
URI: https://hdl.handle.net/10356/154825
ISSN: 2041-6520
DOI: 10.1039/d1sc05876b
Rights: © 2022 The Author(s). Published by the Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported License.
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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