Iron-catalyzed cascade C–C/C–O bond formation of 2,4-dienals with donor–acceptor cyclopropanes: access to functionalized hexahydrocyclopentapyrans

Mishra, Manmath; Verma, Kshitiz; Banerjee, Sonbidya; Punniyamurthy, Tharmalingam

doi:10.1039/d3cc06261a

Cited by 4 publications

(1 citation statement)

References 57 publications

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“…In the last 10–15 years, interest in the chemistry of donor–acceptor cyclopropanes (DACs) has grown sharply [ 1 , 2 , 3 , 4 , 5 ]. Their ring-opening transformations are widely used in organic synthesis to assemble various carbo- and heterocyclic compounds, including natural compounds and their analogs [ 6 , 7 , 8 , 9 , 10 ]. Currently, there are a variety of different types of DAC reactions being reported [ 11 ].…”

Section: Introductionmentioning

confidence: 99%

The TaCl5-Mediated Reaction of Dimethyl 2-Phenylcyclopropane-1,1-dicarboxylate with Aromatic Aldehydes as a Route to Substituted Tetrahydronaphthalenes

Zosim,

Kadikova,

Novikov

et al. 2024

Molecules

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It is found that the reaction of dimethyl 2-phenylcyclopropane-1,1-dicarboxylate with 2 equivalents each of aromatic aldehydes and TaCl5 in 1,2-dichloroethane at 23 °C for 24 h after hydrolysis gives substituted 4-phenyl-3,4-dihydronaphtalene-2,2(1H)-dicarboxylates in good yield. This represents a new type of reactions between 2-arylcyclopropane-1,1-dicarboxylates and aromatic aldehydes, yielding chlorinated tetrahydronaphthalenes with a cis arrangement of the aryl and chlorine substituents in the cyclohexene moiety. A plausible reaction mechanism is proposed.

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Section: Introductionmentioning

confidence: 99%

The TaCl5-Mediated Reaction of Dimethyl 2-Phenylcyclopropane-1,1-dicarboxylate with Aromatic Aldehydes as a Route to Substituted Tetrahydronaphthalenes

Zosim,

Kadikova,

Novikov

et al. 2024

Molecules

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DABCO-Promoted (3 + 2) Annulation of D–A Cyclopropanes with Alkynoates for the Synthesis of Cyclopentenol Derivatives

Liu,

Xue,

Cheng

et al. 2024

J. Org. Chem.

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Efficient synthesis of highly functionalized cyclopentenols with an exocyclic Z double bond was investigated via a (3 + 2) annulation reaction of 2-aroyl-D−A (donor−acceptor) cyclopropanes with alkynoates in the presence of DABCO. This synthetic approach featured a wide range of readily available 2-aroyl-substituted D−A cyclopropanes with diverse functional groups, densely substituted cyclopentenols with two stereogenic centers and an exocyclic double bond in a highly stereocontrolled manner and had operationally simple and mild reaction conditions. Note pubs.acs.org/joc

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Nucleophilic Ring Opening of Donor–Acceptor Cyclopropanes through Umpolung Reactivity of Organochlorophosphines: Phosphine Oxide-Functionalized Boron-Pendanted Compounds

Gopal,

Lamba,

Kushwaha

et al. 2024

Org. Lett.

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We present a novel set of frustrated Lewis pair (FLP) systems that exhibit a remarkable ability to promote the ring opening of donor−acceptor cyclopropanes (DACs). This FLP-promoted protocol offers umpolung reactivity of R 1 R 2 PCl/CN (R 1 , R 2 = aryl, alkyl) toward DACs via nucleophilic ring-opening reactions to provide phosphinated boron-pendanted diester compounds. This novel approach exhibits the dual role of BF 3 •OEt 2 as an activator and a reactant. The resulting compounds were found in both the keto and enol forms, with the majority being in the keto form, according to NMR analysis. The enol form was identified by single-crystal XRD analysis, and DFT calculations indicated that the keto form is more stable than the corresponding enol form.

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Iron-catalyzed cascade C–C/C–O bond formation of 2,4-dienals with donor–acceptor cyclopropanes: access to functionalized hexahydrocyclopentapyrans

Abstract: Iron-catalyzed cascade C-C and C-O bond formation of 2,4-dienals with donor-acceptor cyclopropanes (DACs) has been developed to furnish hexahydrocyclopentapyrans. Optically active DAC can be coupled stereospecifically (>97% ee). Chirality transfer,...

Cited by 4 publications

References 57 publications

The TaCl5-Mediated Reaction of Dimethyl 2-Phenylcyclopropane-1,1-dicarboxylate with Aromatic Aldehydes as a Route to Substituted Tetrahydronaphthalenes

The TaCl5-Mediated Reaction of Dimethyl 2-Phenylcyclopropane-1,1-dicarboxylate with Aromatic Aldehydes as a Route to Substituted Tetrahydronaphthalenes

DABCO-Promoted (3 + 2) Annulation of D–A Cyclopropanes with Alkynoates for the Synthesis of Cyclopentenol Derivatives

Nucleophilic Ring Opening of Donor–Acceptor Cyclopropanes through Umpolung Reactivity of Organochlorophosphines: Phosphine Oxide-Functionalized Boron-Pendanted Compounds

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