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Silylative Reductive Amination of alpha,beta-Unsaturated Aldehydes: AConvenient Synthetic Route to beta-Silylated Secondary Amines

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Title
Silylative Reductive Amination of alpha,beta-Unsaturated Aldehydes: AConvenient Synthetic Route to beta-Silylated Secondary Amines
Author(s)
Eunae Kim; Sehoon Park; Sukbok Chang
Subject
hydrosilylation, ; Lewis acidic borane, ; reductive amination, ; selectivity, ; alpha,beta-unsaturated compounds
Publication Date
2018-04
Journal
CHEMISTRY-A EUROPEAN JOURNAL, v.24, no.22, pp.5765 - 5769
Publisher
WILEY-V C H VERLAG GMBH
Abstract
Described here is a reductive amination/hydrosilylation cascade of alpha,beta-unsaturated aldehydes mediated by a Lewis acidic borane catalyst. The present reaction system provides an one-pot synthetic route towards beta-silylated secondary amines that have not been accessible by other previous catalysis. Comparative (HNMR)-H-1 studies on the silylative reduction of enimines revealed that steric bulkiness of primary amine reactants strongly affects both catalytic efficiency and regioselectivity. This strategy was applicable to a broad range of substrates and amenable to one-pot gram-scale synthesis. Moreover, a diastereoselective introduction of the beta-silyl group was also found to be feasible (d.r. up to 71:29) ⓒ 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
URI
https://pr.ibs.re.kr/handle/8788114/5926
DOI
10.1002/chem.201800958
ISSN
0947-6539
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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