Understanding reactivity and regioselectivity in Diels–Alder reactions of a sugar-derived dienophile bearing two competing EWGs. An experimental and computational study

Giri, German Francisco; Sarotti, Ariel M.; Spanevello, Rolando A.

doi:10.1016/j.carres.2015.07.017

Cited by 2 publications

(1 citation statement)

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“…For these reasons, we undertook a comparative computational and experimental study of Diels–Alder reactions between levoglucosenone and 4‐cyano‐levoglucosenone (Scheme ) with four different dienes: cyclopentadiene, 2‐methyl‐1,3‐butadiene, 2,3‐dimethyl‐1,3‐butadiene and 9‐anthracene methanolmethyl ether that could lead to regioisomeric adducts . The collected experimental and computational data allowed to understand the effect of a β‐cyano substitution in the dienophilic performance of the corresponding enone and predict the reactivity enhancement.…”

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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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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Understanding reactivity and regioselectivity in Diels–Alder reactions of a sugar-derived dienophile bearing two competing EWGs. An experimental and computational study

Cited by 2 publications

References 35 publications

Levoglucosenone and Its New Applications: Valorization of Cellulose Residues

Levoglucosenone and Its New Applications: Valorization of Cellulose Residues

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

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