Tetrahedron letters2022,Vol.1024.DOI:10.1016/j.tetlet.2022.153922

Acceleration effect of mild organocatalytic system 2,2'-biphenol/B(OH)(3) for 2-aza-Cope rearrangement

Sugimoto, Kenji Yoshida, Ryoga Matsuya, Yuji
Tetrahedron letters2022,Vol.1024.DOI:10.1016/j.tetlet.2022.153922

Acceleration effect of mild organocatalytic system 2,2'-biphenol/B(OH)(3) for 2-aza-Cope rearrangement

Sugimoto, Kenji 1Yoshida, Ryoga 1Matsuya, Yuji1
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作者信息

  • 1. Univ Toyama
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Abstract

Organocatalysis by the combination of weak acids, namely, 2,20-biphenol and B(OH)3, for 2-aza-Cope rearrangement is described. Aldehydes and 1,1-diphenyl homoallylamine were converted into the corre-sponding homoallylamines in moderate-to-high yield in the presence of 10 mol% 2,20-biphenol and 30 mol% B(OH)3. In contrast to the conventional 2-aza-Cope rearrangement catalyzed by strong activa-tors, a user-and environment-friendly organocatalytic system was established using a combination of inexpensive, easy-to-handle, non-hazardous, and bench-stable reagents.(c) 2022 Elsevier Ltd. All rights reserved.

Key words

2-aza-Cope rearrangement/Boric acid/22'-biphenol/AZA-COPE REARRANGEMENT/CATALYTIC ASYMMETRIC AMINOALLYLATION/ALPHA-AMINO-ACIDS/ORGANOMETALLIC REAGENTS/CERNUANE-TYPE/DERIVATIVES/ALKALOIDS/ALDEHYDES

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出版年

2022
Tetrahedron letters

Tetrahedron letters

CCR
ISSN:0040-4039
参考文献量38
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