Regio‐ and Stereoselective Synthesis of Cyclopentenones: Intermolecular Pseudo‐Pauson–Khand Cyclization

Barluenga, José; Álvarez‐Fernández, Ana; Suárez‐Sobrino, Ángel L.; Tomás, Miguel

doi:10.1002/anie.201105362

Cited by 30 publications

(13 citation statements)

References 46 publications

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“…In a complementary approach to the various Pauson-Khand routes, Barluenga et al used Fischer carbene complexes as precursors for the co-cyclization with vinyllithium reagents, giving rise to bicyclo[3.3.0]octenones 40 in good yields (Scheme 7). 46 Both chromium and tungsten Fischer carbene complexes could be used. In the case of tungsten carbenes carrying menthyl units, high enantioselectivities were obtained.…”

Section: Methodsmentioning

confidence: 99%

Adventures and Detours in the Synthesis of Hydropentalenes

Deimling

Zens

Park

et al. 2020

Synlett

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Functionalized hydropentalenes (i.e., bicyclo[3.3.0]octanones) constitute important building blocks for natural products and for ligands for asymmetric catalysis. The assembly and tailored functionalization of this convex roof-shaped scaffold is challenging and has motivated a variety of synthetic approaches including our own contributions, which will be presented in this account.1 Introduction2 Biosynthesis of Hydropentalenes3 Hydropentalenes through the Pauson–Khand Reaction4 Hydropentalenes through Transannular Oxidative Cyclization of Cycloocta-1,4-diene5 Functionalization of Bicyclo[3.3.0]octan-1,4-dione to Dodecahydrocyclopenta[a]indenes6 Functionalization of Bicyclo[3.3.0]octan-1,4-diones to Crown Ether Hybrids7 Functionalization of Bicyclo[3.3.0]octan-1,4-dione to Cylindramide8 Tandem Ring-Opening Metathesis/Ring-Closing Metathesis/Cross-Metathesis of Bicyclo[2.2.1]heptanes9 Functionalization of Bicyclo[3.3.0]octan-1,4-dione to Geodin A10 Hydropentalenes through Enantioselective Desymmetrization of Weiss Diketones11 Functionalization of Weiss Diketones by Carbonyl Ene Reactions12 Functionalization of the Weiss Diketone to Cylindramide and Geodin A Core Units13 Biological Properties of Bicyclo[3.3.0]octanes14 Hydropentalenes through Vinylcyclopropane Cyclopentene Rearrangement15 Functionalization of Bicyclo[3.3.0]octanes toward Chiral Dienes16 Miscellaneous Syntheses of Hydropentalenes17 Conclusion and Outlook

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Section: Methodsmentioning

confidence: 99%

Adventures and Detours in the Synthesis of Hydropentalenes

Deimling

Zens

Park

et al. 2020

Synlett

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“…The 2,3‐diaryl cyclopent‐2‐enone scaffold is present in the highly potent COX‐2 inhibitor 4 , as well as in the combretocyclopentenones 5 and related compounds, which exhibit antitumor activity. Moreover, there are few asymmetric methods for the de novo construction of cyclopent‐2‐enones with a quaternary stereocenter at the 5‐position (as in 3 ) . Although our previous work on enantioselective nickel‐catalyzed arylative cyclizations of alkynyl electrophiles showed that ketones and activated alkenes, are competent reaction partners for alkenylnickel species, the ability of less electrophilic esters to undergo analogous cyclizations was less certain.…”

Section: Figurementioning

confidence: 99%

Enantioselective Synthesis of Chiral Cyclopent‐2‐enones by Nickel‐Catalyzed Desymmetrization of Malonate Esters

et al. 2018

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The enantioselective synthesis of highly functionalized chiral cyclopent‐2‐enones by the reaction of alkynyl malonate esters with arylboronic acids is described. These desymmetrizing arylative cyclizations are catalyzed by a chiral phosphinooxazoline/nickel complex, and cyclization is enabled by the reversible E/Z isomerization of alkenylnickel species. The general methodology is also applicable to the synthesis of 1,6‐dihydropyridin‐3(2H)‐ones.

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“…For structures of related 3-Ph substituted cyclopent-2-ene-1ones, see: Zhao et al (2008); Marjani et al (2007Marjani et al ( , 2008; Jedrzejas et al (1996). For leading references on the synthesis and uses of substituted cyclopentenones, see: Gibson et al (2004); Gibson & Mainolfi (2005); Liu et al (2013); Barluenga et al (2012); Varea et al (2012). For materials chemistry applications, see: Peloquin et al (2012); Li et al (2008).…”

Section: Related Literaturementioning

confidence: 99%

3-(4-Bromophenyl)cyclopent-2-en-1-one

Shurdha¹,

Dees²,

Miller³

et al. 2014

Acta Cryst E

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In the title compound, C11H9BrO, the cyclopentenone ring is almost planar with an r.m.s. deviation of 0.0097 Å. The largest inter-ring torsion angles [2.4 (3), 1.3 (3) and 3.53 (2)°] reveal only a very small twist between the rings, and suggest that the two rings are conjugated. The molecule is slightly bowed, as shown by the small dihedral angle between the rings [5.3 (1)°]. The crystal packing pattern consists of parallel sheets that stack parallel to the ac plane. Each sheet consists of molecules that pack side-to-side with the same relative orientation of phenyl and cyclopentenone rings along the a- and c-axis directions. Slipped side-to-side, face-to-face and edge-to-face interactions exist between pairs of sheets with edge-to-edge and edge-to-face O⋯H—C(sp 2) weak hydrogen-bond contacts. A relatively short edge-to-face contact (2.77 Å) also exists between pairs of sheets.

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Regio‐ and Stereoselective Synthesis of Cyclopentenones: Intermolecular Pseudo‐Pauson–Khand Cyclization

Cited by 30 publications

References 46 publications

Adventures and Detours in the Synthesis of Hydropentalenes

Adventures and Detours in the Synthesis of Hydropentalenes

Enantioselective Synthesis of Chiral Cyclopent‐2‐enones by Nickel‐Catalyzed Desymmetrization of Malonate Esters

3-(4-Bromophenyl)cyclopent-2-en-1-one

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