Montmorillonite K-10 promoted synthesis of chiral dioxa-caged compounds derived from levoglucosenone

Zurita, Mariano; Avila, Aylén; Spanevello, Rolando A.; Suárez, Alejandra G.; Sarotti, Ariel M.

doi:10.1016/j.carres.2014.07.019

Cited by 7 publications

(3 citation statements)

References 43 publications

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“…For this reason, we developed a short and efficient methodology for the synthesis of novel chiral dioxa‐caged compounds derived from the cycloaddition adduct from levoglucosenone and simple cyclic dienes. The reaction sequence involves a cascade 3‐step cationic cyclization, which was performed in high yields and selectivities under mild condition with Montmorillonite K‐10 as catalyst (Scheme ) The usefulness of this acidic aluminosilicate catalyst in related semi‐pinacol rearrangements to obtain pyran‐3‐ones was also studied. Differences in the reaction pathways were found for the epimeric alcohols and DFT calculations were used to explain this stereoelectronic effects.…”

Section: Enantiospecific Synthesismentioning

confidence: 99%

Levoglucosenone and Its New Applications: Valorization of Cellulose Residues

et al. 2017

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The need to find sustainable alternatives to reduce the dependence on fossil sources has led to significant research efforts on the conversion of biomass into platform chemicals. Modern organic chemistry requires easily obtainable chiral building blocks that show high chemical versatility for their application in the synthesis of enantiopure compounds. The selective pyrolytic conversion of cellulose or cellulose‐containing materials produces levoglucosenone, a highly functionalized chiral structure. This compound has been innovatively used as a template for the synthesis of key intermediates of biologically active products and for the preparation of chiral auxiliaries, catalysts, and organocatalysts for their application in asymmetric synthesis.

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Section: Enantiospecific Synthesismentioning

confidence: 99%

Levoglucosenone and Its New Applications: Valorization of Cellulose Residues

et al. 2017

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“…The rapid development of LGO chemistry during the last five decades and its applications in medicinal and polymer chemistry are reported in review articles and original publications, which have regularly appeared in recent years [23][24][25][26][27][28][29]. Diverse transformations of LGO were achieved based, among others, on 1,3-dipolar cycloadditions [30][31][32], Diels-Alder reactions [33][34][35], and Michael additions [36][37][38]. For example, in a pioneering work, reactions of 6 with a 'classic', non-fluorinated benzonitrile imine 9 (C(Ph),N(Ph)) nitrile imine were reported to yield a mixture of two re-gioisomeric, fused pyrazoles 7 and 7 (in a ca.…”

Section: Introductionmentioning

confidence: 99%

“…Molecules 2023, 28, x FOR PEER REVIEW 3 of 17 [23][24][25][26][27][28][29]. Diverse transformations of LGO were achieved based, among others, on 1,3-dipolar cycloadditions [30][31][32], Diels-Alder reactions [33][34][35], and Michael additions [36][37][38]. For example, in a pioneering work, reactions of 6 with a 'classic', non-fluorinated benzonitrile imine 9 (C(Ph),N(Ph)) nitrile imine were reported to yield a mixture of two regioisomeric, fused pyrazoles 7 and 7′ (in a ca.…”

Section: Introductionmentioning

confidence: 99%

(3+2)-Cycloadditions of Levoglucosenone (LGO) with Fluorinated Nitrile Imines Derived from Trifluoroacetonitrile: An Experimental and Computational Study

Mlostoń,

Urbaniak,

Palusiak

et al. 2023

Molecules

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The in situ-generated N-aryl nitrile imines derived from trifluoroacetonitrile smoothly undergo (3+2)-cycloadditions onto the enone fragment of the levoglucosenone molecule, yielding the corresponding, five-membered cycloadducts. In contrast to the ‘classic’ C(Ph),N(Ph) nitrile imine, reactions with fluorinated C(CF3),N(Ar) analogues lead to stable pyrazolines in a chemo- and stereoselective manner. Based on the result of X-ray single crystal diffraction analysis, their structures were established as exo-cycloadducts with the location of the N-Ar terminus of the 1,3-dipole at the α-position of the enone moiety. The DFT computation demonstrated that the observed reaction pathway results from the strong dominance of kinetic control over thermodynamic control.

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Bio‐Based Chiral Amines via Aza‐Michael Additions to (–)‐Levoglucosenone Under Aqueous Conditions

et al. 2018

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Chiral amines are highly coveted within the fine‐chemical industry and sustainable synthetic methodologies for their production are of great value. By harnessing the chirality present in cellulose‐derived (–)‐levoglucosenone (LGO), several bio‐based sp3‐rich amines containing up to four chiral centres have been readily prepared under aqueous conditions without using any catalysts, ligands, auxiliaries or resolutions.

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Montmorillonite K-10 promoted synthesis of chiral dioxa-caged compounds derived from levoglucosenone

Cited by 7 publications

References 43 publications

Levoglucosenone and Its New Applications: Valorization of Cellulose Residues

Levoglucosenone and Its New Applications: Valorization of Cellulose Residues

(3+2)-Cycloadditions of Levoglucosenone (LGO) with Fluorinated Nitrile Imines Derived from Trifluoroacetonitrile: An Experimental and Computational Study

Bio‐Based Chiral Amines via Aza‐Michael Additions to (–)‐Levoglucosenone Under Aqueous Conditions

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