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Conjugate addition – enantioselective protonation reactions

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ABSTRACT

The addition of nucleophiles to electron-deficient alkenes represents one of the more general and commonly used strategies for the convergent assembly of more complex structures from simple precursors. In this review the addition of diverse protic and organometallic nucleophiles to electron-deficient alkenes followed by enantioselective protonation is summarized. Reactions are first categorized by the type of electron-deficient alkene and then are further classified according to whether catalysis is achieved with chiral Lewis acids, organocatalysts, or transition metals.

No MeSH data available.


Togni’s enantioselective hydroamination of methacrylonitrile.
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C42: Togni’s enantioselective hydroamination of methacrylonitrile.

Mentions: Togni and co-workers subsequently reported the hydroamination of methacrylonitrile 174 using palladium(II) catalyst 172 (Scheme 42) [72]. Low temperature and bulky aryl groups on the catalyst were necessary to achieve good levels of enantioselectivity. In a later study, their nickel(II) catalyst 171 proved to be much more selective under the same reaction conditions (Scheme 42) [74]. Togni and co-workers also investigated the hydroamination of methacrylonitrile using benzylamine and aniline; however, these substrates gave products with low enantioselectivity (55:45 to 61:29 er).


Conjugate addition – enantioselective protonation reactions
Togni’s enantioselective hydroamination of methacrylonitrile.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC4979737&req=5

C42: Togni’s enantioselective hydroamination of methacrylonitrile.
Mentions: Togni and co-workers subsequently reported the hydroamination of methacrylonitrile 174 using palladium(II) catalyst 172 (Scheme 42) [72]. Low temperature and bulky aryl groups on the catalyst were necessary to achieve good levels of enantioselectivity. In a later study, their nickel(II) catalyst 171 proved to be much more selective under the same reaction conditions (Scheme 42) [74]. Togni and co-workers also investigated the hydroamination of methacrylonitrile using benzylamine and aniline; however, these substrates gave products with low enantioselectivity (55:45 to 61:29 er).

View Article: PubMed Central - HTML - PubMed

ABSTRACT

The addition of nucleophiles to electron-deficient alkenes represents one of the more general and commonly used strategies for the convergent assembly of more complex structures from simple precursors. In this review the addition of diverse protic and organometallic nucleophiles to electron-deficient alkenes followed by enantioselective protonation is summarized. Reactions are first categorized by the type of electron-deficient alkene and then are further classified according to whether catalysis is achieved with chiral Lewis acids, organocatalysts, or transition metals.

No MeSH data available.