Transformation of oxiranes into other oxygen-containing heterocyclic systems

Kas’yan, L. I.; Tarabara, I. N.; Kas’yan, A. O.

doi:10.1007/s11178-005-0001-9

Cited by 13 publications

(1 citation statement)

References 143 publications

(127 reference statements)

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“…Hydrolysis of spiro ‐epoxides [104] has been efficiently applied in the total synthesis of natural α‐(hydroxymethyl)cycloalkanols. It can be performed under acidic or basic conditions and was reported during the total synthesis of numerous compounds.…”

Section: Synthesismentioning

confidence: 99%

Design, Synthesis, and Evaluation of α‐(Hydroxymethyl)cycloalkanols

Nassar

Piva

2021

Eur J Org Chem

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α‐(Hydroxymethyl)cycloalkanols are pervasive structural scaffolds found in natural products and synthetic intermediates with varied biochemical and physicochemical properties. These profiles have driven numerous research groups to the synthesis of such motifs using innovative methodologies. The presence of vicinal diols attached to a cycloalkane makes from these motifs excellent synthetic intermediates for the synthesis of diverse ring systems. This investigation takes an overview of the literature for the occurrence and synthesis of α‐(hydroxymethyl)cycloalkanol derivatives, concentrating on advances in the last two decades.

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Section: Synthesismentioning

confidence: 99%

Design, Synthesis, and Evaluation of α‐(Hydroxymethyl)cycloalkanols

Nassar

Piva

2021

Eur J Org Chem

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Synthesis of Cyclic Carbonates Catalysed by Aluminium Heteroscorpionate Complexes

Martı́nez

Castro‐Osma

Earlam

et al. 2015

Chemistry A European J

105

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New aluminium scorpionate based complexes have been prepared and used for the synthesis of cyclic carbonates from epoxides and carbon dioxide. Bimetallic aluminium(heteroscorpionate) complexes 9-14 were synthesised in very high yields. The single-crystal X-ray structures of 12 and 13 confirm an asymmetric κ(2)-NO-μ-O arrangement in a dinuclear molecular disposition. These bimetallic aluminium complexes were investigated as catalysts for the synthesis of cyclic carbonates from epoxides and carbon dioxide in the presence of ammonium salts. Under the optimal reaction conditions, complex 9 in combination with tetrabutylammonium bromide acts as a very efficient catalyst system for the conversion of both monosubstituted and internal epoxides into the corresponding cyclic carbonates showing broad substrate scope. Complex 9 and tetrabutylammonium bromide is the second most efficient aluminium-based catalyst system for the reaction of internal epoxides with carbon dioxide. A kinetic study has been carried out and showed that the reactions were first order in complex 9 and tetrabutylammonium bromide concentrations. Based on the kinetic study, a catalytic cycle is proposed.

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