Selective Formation of Monoacylated Diols through a Mild Passerini Reaction

Wu, Dan; Li, Jun; Wang, Wei

doi:10.1002/ejoc.201800499

Cited by 7 publications

(3 citation statements)

References 40 publications

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“…Wang and co-workers examined the use of glycoaldehyde derivatives in the Passerini reaction and found that two different regioisomeric monoacylated diols could be attained depending on reaction conditions (Scheme ). The authors suspected that the two different products could arise from divergence in the reaction pathway after formation of the O-acyl imidate. Acyl transfer to the secondary hydroxyl group through a five-membered transition state would provide the monoacylated diol with a free primary hydroxyl group.…”

Section: Condensationsmentioning

confidence: 99%

HFIP in Organic Synthesis

et al. 2022

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1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) is a polar, strongly hydrogen bond-donating solvent that has found numerous uses in organic synthesis due to its ability to stabilize ionic species, transfer protons, and engage in a range of other intermolecular interactions. The use of this solvent has exponentially increased in the past decade and has become a solvent of choice in some areas, such as C–H functionalization chemistry. In this review, following a brief history of HFIP in organic synthesis and an overview of its physical properties, literature examples of organic reactions using HFIP as a solvent or an additive are presented, emphasizing the effect of solvent of each reaction.

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Section: Condensationsmentioning

confidence: 99%

HFIP in Organic Synthesis

et al. 2022

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“…To evaluate the most appropriate reaction conditions for the synthesis of α-acyloxy ketones, an initial search for the best solvent was carried out in a batch microwave (MW) preliminary optimization using solvents typically applied in Passerini reactions (Wu et al, 2018) (Table 1) and considering our previous experience in MW-mediated MCR reactions (Barreto et al, 2011a,b, 2014; Salvador et al, 2015; Barreto and Andrade, 2018, 2019). Formation of the Passerini product in toluene at 110°C was not observed probably be due to the low microwave dielectric heating property of this solvent (Gabriel et al, 1998; Kappe et al, 2012) (entry 1).…”

Section: Resultsmentioning

confidence: 99%

A Mild, Fast, and Scalable Synthesis of Substituted α-Acyloxy Ketones via Multicomponent Reaction Using a Continuous Flow Approach

Salvador

Andrade

2019

Front. Chem.

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A continuous flow approach for the synthesis of α-acyloxy ketone derivatives from the corresponding arylglyoxals, isocyanides, and carboxylic acids is described. The target products were obtained in excellent yields in short residence times and with high purities via the first transcription of the microwave-to-flow paradigm to the isocyanide-based Passerini reaction. Furthermore, this methodology allowed a 10-fold scale-up using the same experimental conditions initially established.

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“…The Passerini three-component reaction (P-3CR) 13 was developed aer Passerini's discovery of the reaction between isocyanides, aldehydes, and carboxylic acids to produce a-acyloxy carboxamides in 1921. 14,15 It has since grown to be a potent tool in combinatorial chemistry and hetero cyclic chemistry for drug discovery as well as natural product synthesis. [16][17][18] Passerini reaction has been known for over 80 years, little is known about the scope of carbonyl-type electrophiles that undergo the reaction (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%