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• W3181635231 abstract "The base-promoted α-alkylation of N-((S)-1-arylethyl)azetidine-2-carbonitriles 3via formation of their N-borane complexes 4 was investigated. For example, treatment of diastereomerically pure borane N-((S)-1'-(4''-methoxyphenyl)ethyl)azetidine-2-carbonitrile complex (1S,2S,1'S)-4b with 1.2 equivalents of LDA at -78 °C followed by 1.3 equivalents of benzyl bromide at -78 °C and warming to room temperature produced α-benzylated (2S,1'S)-5ba in 72% yield and (2R,1'S)-5ba in 2% yield. A mechanism for this diastereoselective α-alkylation was proposed. Our method enables the production of optically active 2-substituted azetidine-2-carbonitriles, such as α-benzylated (S)-10a and (R)-10a, starting from commercially available (S)-(1-(4-methoxyphenyl)ethyl)amine." @default.
• W3181635231 created "2021-07-19" @default.
• W3181635231 creator A5055947731 @default.
• W3181635231 creator A5075826122 @default.
• W3181635231 date "2021-01-01" @default.
• W3181635231 modified "2023-09-27" @default.
• W3181635231 title "Synthesis of optically active 2-substituted azetidine-2-carbonitriles from chiral 1-arylethylamine <i>via</i> α-alkylation of <i>N</i>-borane complexes" @default.
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• W3181635231 doi "https://doi.org/10.1039/d1ra04585g" @default.
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