Stereoselective Shi-type epoxidation with 3-oxo-4,6-<i>O</i>-benzylidene pyranoside catalysts: unveiling the role of carbohydrate skeletons

Imperio, Daniela; Valloni, Filippo; Caprioglio, Diego; Minassi, Alberto; Casali, Emanuele; Panza, Luigi

doi:10.1039/d4ra03011g

RSC Adv.

2024

DOI: 10.1039/d4ra03011g

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Stereoselective Shi-type epoxidation with 3-oxo-4,6-O-benzylidene pyranoside catalysts: unveiling the role of carbohydrate skeletons

Daniela Imperio,

Filippo Valloni,

Diego Caprioglio

et al.

Abstract: Sugar-derived chiral ketones are capable of reversing stereoselectivity in Shi-type epoxidation.

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Development of Organocatalytic Darzens Reactions Exploiting the Cyclopropenimine Superbase

Lops,

Pasquato,

Pengo

2024

Molecules

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A truly organocatalytic approach to the Darzens reaction affording α,β-epoxy carbonyl compounds in good yields was developed taking advantage of the high basic strength and low nucleophilicity of cyclopropenimine superbases. The catalytic active free base can easily be generated in situ from its hydrochloride salt and maintained in the active deprotonated form by performing the reactions in a heterogeneous reaction system in the presence of excess potassium carbonate as a sacrificial base.

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Development of Organocatalytic Darzens Reactions Exploiting the Cyclopropenimine Superbase

Lops,

Pasquato,

Pengo

2024

Molecules

View full text Add to dashboard Cite

show abstract

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Stereoselective Shi-type epoxidation with 3-oxo-4,6-O-benzylidene pyranoside catalysts: unveiling the role of carbohydrate skeletons

Abstract: Sugar-derived chiral ketones are capable of reversing stereoselectivity in Shi-type epoxidation.

Cited by 1 publication

References 33 publications

Development of Organocatalytic Darzens Reactions Exploiting the Cyclopropenimine Superbase

Development of Organocatalytic Darzens Reactions Exploiting the Cyclopropenimine Superbase

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