1,2-Amino Alcohols via Cr/Photoredox Dual Catalyzed Addition of α-Amino Carbanion Equivalents to Carbonyls,Journal of the American Chemical Society

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1,2-Amino Alcohols via Cr/Photoredox Dual Catalyzed Addition of α-Amino Carbanion Equivalents to Carbonyls
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2020-01-10 , DOI: 10.1021/jacs.9b12053
J Luca Schwarz ₁ , Roman Kleinmans ₁ , Tiffany O Paulisch ₁ , Frank Glorius ₁

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Herein, we report the synthesis of protected 1,2-amino alcohols starting from carbonyl compounds (mostly aldehydes) and α-silyl amines. The reaction is enabled by a Cr/photoredox dual catalytic system that allows the in situ generation of α-amino carbanion equivalents which act as nucleophiles. The unique nature of this reaction was demonstrated through the aminoalkylation of ketones and an acyl silane, classes of electrophiles that were previously unreactive towards addition of alkyl-Cr reagents. Overall this reaction broadens the scope of Cr-mediated carbonyl alkylations and discloses an underex-plored retrosynthetic strategy for the synthesis of 1,2-amino alcohols.

中文翻译：

1,2-氨基醇通过 Cr/Photoredox 双催化将 α-氨基碳负离子等价物加成到羰基

在此，我们报告了从羰基化合物（主要是醛）和 α-甲硅烷基胺开始合成受保护的 1,2-氨基醇。该反应由 Cr/光氧化还原双催化系统实现，该系统允许原位生成充当亲核试剂的 α-氨基碳负离子等价物。通过酮和酰基硅烷的氨基烷基化证明了该反应的独特性质，这些亲电试剂以前对添加烷基-Cr 试剂不反应。总的来说，该反应拓宽了 Cr 介导的羰基烷基化的范围，并揭示了一种尚未充分探索的用于合成 1,2-氨基醇的逆合成策略。

更新日期：2020-01-10

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