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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.


Darses and Genet’s addition of potassium organotrifluoroborates to α-aminoacrylates.
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C12: Darses and Genet’s addition of potassium organotrifluoroborates to α-aminoacrylates.

Mentions: Darses and Genet reported the highly enantioselective Rh-catalyzed addition of potassium organotrifluoroborates 49 to α-aminoacrylates 52 to access phenylalanine derivatives 54 (Scheme 12) [33]. The authors identified guaiacol (53) as the optimal proton source, observing the general trend that less acidic phenols led to an increase in enantioselectivity. A wide range of aryltrifluoroborates were efficient substrates for the reaction to provide the products in good yield and enantioselectivity. Increasing the steric bulk of the ester (R2 = iPr, t-Bu) decreased the yield of the reaction but did not impact its enantioselectivity.


Conjugate addition – enantioselective protonation reactions
Darses and Genet’s addition of potassium organotrifluoroborates to α-aminoacrylates.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

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

C12: Darses and Genet’s addition of potassium organotrifluoroborates to α-aminoacrylates.
Mentions: Darses and Genet reported the highly enantioselective Rh-catalyzed addition of potassium organotrifluoroborates 49 to α-aminoacrylates 52 to access phenylalanine derivatives 54 (Scheme 12) [33]. The authors identified guaiacol (53) as the optimal proton source, observing the general trend that less acidic phenols led to an increase in enantioselectivity. A wide range of aryltrifluoroborates were efficient substrates for the reaction to provide the products in good yield and enantioselectivity. Increasing the steric bulk of the ester (R2 = iPr, t-Bu) decreased the yield of the reaction but did not impact its enantioselectivity.

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.