Diastereoselective Synthesis of Tetrahydrofurans via Palladium(0)-Catalyzed [3 + 2] Cycloaddition of Vinylcyclopropanes and Aldehydes

Parsons, Andrew T.; Campbell, Matthew; Johnson, Jeffrey S.

doi:10.1021/ol800819h

Cited by 156 publications

(81 citation statements)

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“…163 This reactivity is allowed by a Lewis acid activation, or by palladium catalysis. 164,165 The oxolanes obtained usually display a good cis-2,5-stereochemistry. An enantioselective version of this transformation was proposed by the group of Johnson, by M A N U S C R I P T A C C E P T E D ACCEPTED MANUSCRIPT 32 means of deracemization of the starting aryl or vinyl cyclopropane through a dynamic kinetic asymmetric transformation.…”

Section: Thf Synthesis By Simultaneous C-o and C-c Bond Formationmentioning

confidence: 99%

Recent advances in the synthesis of tetrahydrofurans and applications in total synthesis

et al. 2016

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Mousseron. His research interests include the total synthesis of oxygenated cyclic and non cyclic metabolites of polyunsaturated fatty acids, mainly leukotrienes, iso-, phyto-and neuroprostanes, as well as dihydroxylated PUFAs and more recently lipophenols and the understanding of the role of such bioactive lipids and lipophenols by developing collaborations with chemists, biochemists, biologists and clinicians across the world. Jean-Marie Galano studied chemistry at Paul Cézanne Université Marseille and obtained his PhD under the supervision of Honoré Monti in 2001. He then moved to the University of Oxford to pursue a postdoctoral fellowship with David H. Hodgson on the development of new methods for the total synthesis of natural products. In October 2005 he joined the CNRS as a Chargé de Recherche at Université of Montpellier. His research focuses on the total synthesis and discovery of new lipid metabolites, and to discover their potential implications in human health. AbstractMany natural products contain tetrahydrofuran (THF) moieties. Those molecules, often biologically active, may be structurally diverse, e.g. cis or trans THF, mono-, di-, tri-or tetrasubstituted on the furan ring. Thus, the construction of THF is of great interest for the community of organic chemists; especially in developing new methodologies, and applying them in the total synthesis of natural products. The aim of this review is to report recent advances in the field of THF synthesis, as well as the application of these methods to the synthesis of bioactive compounds.

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Section: Thf Synthesis By Simultaneous C-o and C-c Bond Formationmentioning

confidence: 99%

Recent advances in the synthesis of tetrahydrofurans and applications in total synthesis

et al. 2016

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“…[28] In the case of vinyl-substituted cyclopropanes, activation with a palladium catalyst became possible, due to the formation of a stable -allyl intermediate. [29] The broad applicability of the method was further demonstrated in the total synthesis of natural products, including (+)-virgatusin, [30] (+)-polyanthellin A [31][32] and (+)-isatisine A [33][34] (Figure 7.1). Finally, Wang and coworkers developed intramolecular variations of this reaction to give both fused and bridged polycyclic systems and applied the method to a formal synthesis of platensimycin.…”

Section: C-o Bond Formationmentioning

confidence: 99%

“…[191] This reaction proceeded also with C-N cleavage, but with opposite regioselectivity and high diastereoselectivity. As the trifluoromethyl group is not able to stabilize a carbocation 29 intermediate, the reaction starts most probably by a nucleophilic SN 2 -like attack of the carbonyl on the less substituted carbon of the aziridine.…”

Section: Formal [3+1] Cycloadditionsmentioning

confidence: 99%

Synthesis of Saturated Heterocycles via Metal-Catalyzed Formal Cycloaddition Reactions That Generate a C–N or C–O Bond

Waser

2013

Topics in Heterocyclic Chemistry

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In this section, the synthesis of saturated N-and O-heterocycles via formal cycloaddition is presented. The main focus is on metal-catalyzed reactions involving C-C or C-X  bond cleavage in three-or four-membered rings. After a fast presentation of pioneering works, the important breakthroughs of the last two decades are presented. The section starts with reactions involving three-membered rings. Formal [3+2] cycloadditions of donor-acceptor-substituted cyclopropanes and methylenecyclopropanes with carbonyls and imines are important methods to access tetrahydrofuran and pyrrolidine heterocycles. Formal [3+3] cycloadditions have emerged more recently. On the other hand, reactions of epoxides and aziridines with carbon monoxide or cumulenes are now well-established method to access heterocycles. These processes have been completed more recently with cycloaddition with olefins, carbonyls and imines. The section ends with the emerging field of four-membered ring activation for cycloaddition with  systems. This is the peer reviewed version of the following article: Top. Heterocycl. Chem. 2013, 32, 225, which The discovery of classical cycloaddition reactions, such as the (hetero) DielsAlder and 1,3-dipolar cycloadditions, has contributed tremendously to a more efficient access towards both carbocycles and heterocycles. The introduction of the term cycloaddition was necessary to distinguish these new types of reactions from previously discovered processes leading to cyclic structures, such as the famous Robinson annulation. In principle, each cycloaddition can be considered as a special case of the more general annulation process, but from which point on an annulation can be called a cycloaddition has been the topic of intensive discussions for decades, and is still not settled today. In 1968, Huisgen proposed a set of rules for the definition of cycloaddition, and the two first are still largely recognized as prerequisite: Although the rule that all the atoms of the starting materials have to be included in the product is not explicitly included in the definition, this requirement is usually recognized by most organic chemists. Even if electrocyclic cyclization processes were included in the original definition of Huisgen, the term cycloaddition is mostly used today for those reactions proceeding via the formation of at least two new bonds. Nevertheless, several researchers think that the term cycloaddition should be more strictly limited to reactions involving a continuous overlap of  electrons, and consequently allowing a concerted process. In fact, in his seminal publication, Huisgen already introduced further rules, in particular rule number 3, which explicitly stated that cycloadditions should not involve the cleavage of sigma bonds: -Huisgen Rule 3: "Cycloadditions do not involve the cleavage of  bonds." Unfortunately, in the same publication, Huisgen also described several reactions proceeding via -bond cleavage as cycloaddition. To solve this definition dilemma, several researchers have used th...

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“…13 Reaction of this cyclopropane with commercially available β,2-dinitrostyrene ( 1 1 ) under conditions similar to those developed by Tsuji resulted in the formation of vinylcyclopentane 12 in 60% yield as a mixture of two inseparable diastereomers, (Scheme 3). 10 Upon zinc reduction of the diastereomeric mixture and in situ lactamization, two separable dihydroquinolinone products, 13a and 13b were obtained in 79% yield.…”

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confidence: 95%

A Palladium-Catalyzed Vinylcyclopropane (3 + 2) Cycloaddition Approach to the Melodinus Alkaloids

2011

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Diastereoselective Synthesis of Tetrahydrofurans via Palladium(0)-Catalyzed [3 + 2] Cycloaddition of Vinylcyclopropanes and Aldehydes

Cited by 156 publications

References 51 publications

Recent advances in the synthesis of tetrahydrofurans and applications in total synthesis

Recent advances in the synthesis of tetrahydrofurans and applications in total synthesis

Synthesis of Saturated Heterocycles via Metal-Catalyzed Formal Cycloaddition Reactions That Generate a C–N or C–O Bond

A Palladium-Catalyzed Vinylcyclopropane (3 + 2) Cycloaddition Approach to the Melodinus Alkaloids

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