Enantioselective α‐Carbonylative Arylation for Facile Construction of Chiral Spirocyclic β,β′‐Diketones

Wu, Ting; Zhou, Qinghai; Tang, Wenjun

doi:10.1002/anie.202101668

Cited by 29 publications

(12 citation statements)

References 94 publications

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“…Recently, Pd-catalyzed carbonylation reactions have also been employed in α-arylation reactions implemented for the construction of stereogenic quaternary carbons [78]. Tang and co-workers [79] developed the enantioselective α-carbonylative arylation for the production of chiral spirocyclic β,β′-diketones. Good yields and high enantioselectivities (up to 96% ee) were achieved when Pd 2 (dba) 3 was used as the catalyst and an ethylene-bridged chiral bisphospholane, ((R, R)-Ph-BPE), was used as ligand.…”

Section: Other Palladium-catalyzed Asymmetric Carbonylationsmentioning

confidence: 99%

Palladium-catalyzed enantioselective carbonylation reactions

Peng

Liu

et al. 2022

Sci. China Chem.

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Carbonylation, one of the most powerful approaches to the preparation of carbonylated compounds, has received significant attention from researchers active in various fields. Indeed, impressive progress has been made on this subject over the past few decades. Among the various types of carbonylation reactions, asymmetric carbonylation is a straightforward methodology for constructing chiral compounds. Although rhodium-catalyzed enantioselective hydroformylations have been discussed in several elegant reviews, a general review on palladium-catalyzed asymmetric carbonylations is still missing. In this review, we summarize and discuss recent achievements in palladium-catalyzed asymmetric carbonylation reactions. Notably, this review’s contents are categorized by reaction type.

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Section: Other Palladium-catalyzed Asymmetric Carbonylationsmentioning

confidence: 99%

Palladium-catalyzed enantioselective carbonylation reactions

Peng

Liu

et al. 2022

Sci. China Chem.

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“…Metal catalysts have also been employed for the preparation of 1,3-diketones. One example has been recently described for the preparation of chiral spirocyclic β,β'-diketones (102) [121] through a palladium-catalyzed α-carbonylative arylation. Thus, 2-(2-bromobenzyl)-3,4-dihydronaphthalen-1(2H)-one (101) was treated with CO at 105 • C in diglyme in the presence of Pd 2 dba 3 (2.5 mol%) and a phosphorous ligand (II) using NaO t Bu as base as 4 Å MS as an additive (Scheme 17).…”

Section: Synthesis Of 13-diketones Using Metal-based Catalystsmentioning

confidence: 99%

Recent Developments in the Synthesis of β-Diketones

Gonzalo

Alcántara

2021

Pharmaceuticals

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Apart from being one of the most important intermediates in chemical synthesis, broadly used in the formation of C–C bonds among other processes, the β-dicarbonyl structure is present in a huge number of biologically and pharmaceutically active compounds. In fact, mainly derived from the well-known antioxidant capability associated with the corresponding enol tautomer, β-diketones are valuable compounds in the treatment of many pathological disorders, such as cardiovascular and liver diseases, hypertension, obesity, diabetes, neurological disorders, inflammation, skin diseases, fibrosis, or arthritis; therefore, the synthesis of these structures is an area of overwhelming interest for organic chemists. This paper is devoted to the advances achieved in the last ten years for the preparation of 1,3-diketones, using different chemical (Claisen, hydration of alkynones, decarboxylative coupling) or catalytic (biocatalysis, organocatalytic, metal-based catalysis) methodologies: Additionally, the preparation of branched β-dicarbonyl compounds by means of α-functionalization of non-substituted 1,3-diketones are also discussed.

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“…The absolute configurations of 2 n and 2 ae were determined by X-ray crystallography. [15] The absolute configurations of 2 b-v were assigned by analogy on the basis of 2 n. The absolute configurations of 2 w-z, 2 aa-af were assigned by analogy on the basis of 2 ae. Angewandte Chemie Zuschriften (Scheme 3).…”

Section: Angewandte Chemiementioning

confidence: 99%