Synthetic Studies Towards the Synthesis of 6-Substituted 3-Fluoro-5,6-dihydropyran-2-ones

Mandal, Samir; Sarkar, Apurba; Chakraborty, Partha; Chattopadhyay, Ashoke P.

doi:10.1055/s-0036-1588534

Cited by 6 publications

(5 citation statements)

References 11 publications

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“…For the synthesis of 192, which are 3-fluoro analogs of pharmacologically important 6-substituted 5,6-dihydropyran-2ones, Mandal et al [75] considered the Julia-Kocienski reaction as the key step (Scheme 35). A preliminary study with aldehyde 189 a helped to determine the optimal conditions regarding the base, solvent and reaction temperature (a combination of Cs 2 CO 3 and DCM at room temperature).…”

Section: Methodologies and Other Casesmentioning

confidence: 99%

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Julia‐Kocienski Olefination in the Synthesis of Trisubstituted Alkenes: Recent Progress

Ouzounthanasis,

Rizos,

Koumbis

2023

Eur J Org Chem

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Julia‐Kocienski olefination, a coupling reaction between a carbonyl component and a sulfone partner, has been emerged as a powerful synthetic tool in the preparation of several organic compounds. A number of interesting examples involving particularly the preparation of trisubstituted alkenes along with important observations regarding the stereoselectivity of those reactions have been recently reported. This reviewing work covers the literature for the period 2016‐2022 and describes in a comprehensive way the progress and developments of Julia‐Kocienski olefination application in the synthesis of trisubstituted alkenes which serve as precursors of natural products and their analogs as well of pharmaceutically interesting/biologically important compounds. Moreover, key methodology results dealing with the investigation of the optimum conditions and stereoselectivities and new modifications and approaches are discussed.

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Section: Methodologies and Other Casesmentioning

confidence: 99%

“…For the synthesis of 192 , which are 3‐fluoro analogs of pharmacologically important 6‐substituted 5,6‐dihydropyran‐2‐ones, Mandal et al [75] . considered the Julia‐Kocienski reaction as the key step (Scheme 35).…”

Section: Synthesis Of Trisubstituted Alkenes Via Julia‐kocienski Olef...mentioning

confidence: 99%

Julia‐Kocienski Olefination in the Synthesis of Trisubstituted Alkenes: Recent Progress

Ouzounthanasis,

Rizos,

Koumbis

2023

Eur J Org Chem

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“…A new synthetic approach has been introduced for creating 6‐substituted‐3‐fluoro‐5,6‐dihydropyran‐2‐ones by employing Julia‐Kocienski olefination [75] . The aldehyde 275 was prepared by the hydroxylation of 274 followed by diol cleavage using NaIO 4 in 1,4‐dioxane/H 2 O as solvent.…”

Section: Synthetic Methodologiesmentioning

confidence: 99%

“…A new synthetic approach has been introduced for creating 6-substituted-3-fluoro-5,6-dihydropyran-2-ones by employing Julia-Kocienski olefination. [75] The aldehyde 275 was prepared by the hydroxylation of 274 followed by diol cleavage using NaIO 4 in 1,4-dioxane/H 2 O as solvent. The Julia-Kocienski olefination of sulfone 276 with the intermediate product 275 afforded a mixture of 277 and 278 (Scheme 52).…”

Section: Chemistryselectmentioning

confidence: 99%

Recent Applications and Trends in the Julia‐Kocienski Olefination

Rinu¹,

Radhika²,

Anilkumar³

2022

ChemistrySelect

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The Julia-Kocienski (J-K) olefination is a modified version of Julia-Lythgoe olefination. In this reaction, an aldehyde or ketone is coupled with heterocycle-bearing sulfone in the presence of a strong base to yield alkene. It has shown wide application in the synthesis of olefinic fragments in natural product synthesis. The Julia-Kocienski olefination is one of the most efficient protocols for the synthesis of E-alkenes. Nowa-days, a variety of natural products were synthesised by using the Julia-Kocienski olefination as the key step, and several developments and modifications were witnessed in this area. This review comprehends the recent developments and achievements in Julia-Kocienski olefination along with its application in natural product synthesis covering literature from 2016 to 2021.

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“…The few reports in which this particular donor aldehyde is employed have encountered severe limita-tions in the scope of substrates to nonenolizable, typically electron-poor acceptor aldehydes (1,13,14). Another drawback is the intrinsic lability (15) of the products obtained by these methods, which frequently require protection via O-silylation of the b-hydroxy group after direct cross-aldol reactions (16), or in situ derivatization of the valuable aldehyde moiety by acetal formation (14) or reduction (1,13). By contrast, the single addition products of the Mukaiyama aldol reaction are appreciably more stable and can be readily isolated by conventional purification methods when silyl groups larger than trimethylsilyl are employed.…”

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confidence: 99%

Confined acids catalyze asymmetric single aldolizations of acetaldehyde enolates

Schreyer

Kaib

Wakchaure

et al. 2018

Science

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Reactions that form a product with the same reactive functionality as that of one of the starting compounds frequently end in oligomerization. As a salient example, selective aldol coupling of the smallest, though arguably most useful, enolizable aldehyde, acetaldehyde, with just one partner substrate has proven to be extremely challenging. Here, we report a highly enantioselective Mukaiyama aldol reaction with the simple triethylsilyl (TES) andtert-butyldimethylsilyl (TBS) enolates of acetaldehyde and various aliphatic and aromatic acceptor aldehydes. The reaction is catalyzed by recently developed, strongly acidic imidodiphosphorimidates (IDPi), which, like enzymes, display a confined active site but, like small-molecule catalysts, have a broad substrate scope. The process is scalable, fast, efficient (0.5 to 1.5 mole % catalyst loading), and greatly simplifies access to highly valuable silylated acetaldehyde aldols.

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Synthetic Studies Towards the Synthesis of 6-Substituted 3-Fluoro-5,6-dihydropyran-2-ones

Abstract: The synthesis of 6-substituted 3-fluoro-5,6-dihydropyran-2-ones under mild conditions is described. The key step of the synthesis involves a Julia–Kocienski olefination.

Cited by 6 publications

References 11 publications

Julia‐Kocienski Olefination in the Synthesis of Trisubstituted Alkenes: Recent Progress

Julia‐Kocienski Olefination in the Synthesis of Trisubstituted Alkenes: Recent Progress

Recent Applications and Trends in the Julia‐Kocienski Olefination

Confined acids catalyze asymmetric single aldolizations of acetaldehyde enolates

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