Silylative Reductive Amination of α,β-Unsaturated Aldehydes: A Convenient Synthetic Route to β-Silylated Secondary Amines

Eunae Kim; Sehoon Park; Sukbok Chang

doi:10.1002/chem.201800958

Silylative Reductive Amination of α,β-Unsaturated Aldehydes: A Convenient Synthetic Route to β-Silylated Secondary Amines

Eunae Kim, Sehoon Park^*, Sukbok Chang

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

23 Scopus citations

Abstract

Described here is a reductive amination/hydrosilylation cascade of α,β-unsaturated aldehydes mediated by a Lewis acidic borane catalyst. The present reaction system provides an one-pot synthetic route towards β-silylated secondary amines that have not been accessible by other previous catalysis. Comparative ¹H NMR 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 β-silyl group was also found to be feasible (d.r. up to 71:29).

Original language	English
Pages (from-to)	5765-5769
Number of pages	5
Journal	Chemistry - A European Journal
Volume	24
Issue number	22
DOIs	https://doi.org/10.1002/chem.201800958
State	Published - 17 Apr 2018
Externally published	Yes

Keywords

Lewis acidic borane
hydrosilylation
reductive amination
selectivity
α,β-unsaturated compounds

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10.1002/chem.201800958

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title = "Silylative Reductive Amination of α,β-Unsaturated Aldehydes: A Convenient Synthetic Route to β-Silylated Secondary Amines",

abstract = "Described here is a reductive amination/hydrosilylation cascade of α,β-unsaturated aldehydes mediated by a Lewis acidic borane catalyst. The present reaction system provides an one-pot synthetic route towards β-silylated secondary amines that have not been accessible by other previous catalysis. Comparative 1H NMR 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 β-silyl group was also found to be feasible (d.r. up to 71:29).",

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doi = "10.1002/chem.201800958",

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AU - Chang, Sukbok

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Y1 - 2018/4/17

N2 - Described here is a reductive amination/hydrosilylation cascade of α,β-unsaturated aldehydes mediated by a Lewis acidic borane catalyst. The present reaction system provides an one-pot synthetic route towards β-silylated secondary amines that have not been accessible by other previous catalysis. Comparative 1H NMR 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 β-silyl group was also found to be feasible (d.r. up to 71:29).

AB - Described here is a reductive amination/hydrosilylation cascade of α,β-unsaturated aldehydes mediated by a Lewis acidic borane catalyst. The present reaction system provides an one-pot synthetic route towards β-silylated secondary amines that have not been accessible by other previous catalysis. Comparative 1H NMR 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 β-silyl group was also found to be feasible (d.r. up to 71:29).

KW - Lewis acidic borane

KW - hydrosilylation

KW - reductive amination

KW - selectivity

KW - α,β-unsaturated compounds

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Silylative Reductive Amination of α,β-Unsaturated Aldehydes: A Convenient Synthetic Route to β-Silylated Secondary Amines

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Keywords

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