Publication

Asymmetric (CpRh)-Rh-x(III)-Catalyzed Acrylic Acid C-H Functionalization with Allenes Provides Chiral gamma-Lactones

Nicolai Cramer, Shouguo Wang
2020
Journal Articles

Abstract

A chiral cyclopentadienyl (Cp-x) ligand featuring the semi-saturated H8-binaphthyl backbone as the chiral element was developed. Its application potential was demonstrated by (CpRhIII)-Rh-x-catalyzed C-H bond functionalization of acryl acids and allenes, exhibiting superior catalytic performance compared to other Cp-x ligands. The outlined enantioselective [4 + 1]-annulation process results in synthetically attractive alpha, beta-unsaturated gamma-lactones having an allylic stereogenic center, which were obtained in enantioselectivities of up to 99:1 enantiomeric ratio.

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https://infoscience.epfl.ch/entities/publication/895a80f0-cc80-431e-a9e5-f4b6e9a88688

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Nicolai Cramer, Shouguo Wang
2020
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/895a80f0-cc80-431e-a9e5-f4b6e9a88688

About this result

Related concepts (22)

Metal–organic framework

Metal–organic frameworks (MOFs) are a class of compounds consisting of metal clusters (also known as SBUs) coordinated to organic ligands to form one-, two-, or three-dimensional structures. The organic ligands included are sometimes referred to as "struts" or "linkers", one example being 1,4-benzenedicarboxylic acid (BDC). More formally, a metal–organic framework is an organic-inorganic porous extended structure. An extended structure is a structure whose sub-units occur in a constant ratio and are arranged in a repeating pattern.

Α,β-Unsaturated carbonyl compound

α,β-Unsaturated carbonyl compounds are organic compounds with the general structure (O=CR)−Cα=Cβ-R. Such compounds include enones and enals. In these compounds the carbonyl group is conjugated with an alkene (hence the adjective unsaturated). Unlike the case for carbonyls without a flanking alkene group, α,β-unsaturated carbonyl compounds are susceptible to attack by nucleophiles at the β-carbon. This pattern of reactivity is called vinylogous. Examples of unsaturated carbonyls are acrolein (propenal), mesityl oxide, acrylic acid, and maleic acid.

Acyl group

In chemistry, an acyl group is a moiety derived by the removal of one or more hydroxyl groups from an oxoacid, including inorganic acids. It contains a double-bonded oxygen atom and an organyl group () or hydrogen in the case of formyl group (). In organic chemistry, the acyl group (IUPAC name alkanoyl if the organyl group is alkyl) is usually derived from a carboxylic acid, in which case it has the formula , where R represents an organyl group or hydrogen.

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