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Ketene Aminal Phosphates: Competent Substrates for Enantioselective Pd(0)-Catalyzed C-H Functionalizations

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Nicolai Cramer, Daria Grosheva
2017

Abstract

Enantioselective Pd(0)-catalyzed C-H functionalizations of ketene aminal phosphates provide isoindoline scaffolds with high enantioselectivity at ambient temperature. The high level of enantiocontrol is enabled by a tailored monodentate electron-rich phosphine ligand featuring a point chiral phospholane module and a bulky atropchiral binaphthyl backbone.

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https://infoscience.epfl.ch/entities/publication/4e7f6b08-db07-47a3-b074-39067205639f

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Related concepts (4)

Enantioselective synthesis

Enantioselective synthesis, also called asymmetric synthesis, is a form of chemical synthesis. It is defined by IUPAC as "a chemical reaction (or reaction sequence) in which one or more new elements of chirality are formed in a substrate molecule and which produces the stereoisomeric (enantiomeric or diastereomeric) products in unequal amounts." Put more simply: it is the synthesis of a compound by a method that favors the formation of a specific enantiomer or diastereomer.

Cross-coupling reaction

In organic chemistry, a cross-coupling reaction is a reaction where two different fragments are joined. Cross-couplings are a subset of the more general coupling reactions. Often cross-coupling reactions require metal catalysts. One important reaction type is this: (R, R' = organic fragments, usually aryle; M = main group center such as Li or MgX; X = halide) These reactions are used to form carbon–carbon bonds but also carbon-heteroatom bonds. Cross-coupling reaction are a subset of coupling reactions.

Stille reaction

The Stille reaction is a chemical reaction widely used in organic synthesis. The reaction involves the coupling of two organic groups, one of which is carried as an organotin compound (also known as organostannanes). A variety of organic electrophiles provide the other coupling partner. The Stille reaction is one of many palladium-catalyzed coupling reactions. Allyl, alkenyl, aryl, benzyl,acyl halides (Cl, Br, I), pseudohalides (OTf, OPO(OR)2), OAc The R1 group attached to the trialkyltin is normally sp2-hybridized, including vinyl, and aryl groups.

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