Selective Wacker type oxidation of a macrocyclic diene to the corresponding monounsaturated ketone used as fragrance

Brunzel, Tom; Heppekausen, Johannes; Panten, Johannes; Köckritz, Angela

doi:10.1039/c9ra04971a

Cited by 1 publication

(1 citation statement)

References 42 publications

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“…The rearrangement reactions of alkenes and alkynes have been used for the synthesis of both acyclic and cyclic fragrances [ 96 , 97 , 98 , 99 ], and may be included as the origin of some natural fragrances [ 100 ]. As a classic example, ionones can be synthesized via acid-promoted carbocation rearrangement and cyclization from the polyene precursor pseudoionone, which can be easily obtained via the condensation of citral and acetone [ 52 ].…”

Section: Synthesis Of Fragrances Via Rearrangement or Isomerizationmentioning

confidence: 99%

Synthesis of Cyclic Fragrances via Transformations of Alkenes, Alkynes and Enynes: Strategies and Recent Progress

Lin¹,

Huang²,

Ouyang³

et al. 2022

Molecules

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With increasing demand for customized commodities and the greater insight and understanding of olfaction, the synthesis of fragrances with diverse structures and odor characters has become a core task. Recent progress in organic synthesis and catalysis enables the rapid construction of carbocycles and heterocycles from readily available unsaturated molecular building blocks, with increased selectivity, atom economy, sustainability and product diversity. In this review, synthetic methods for creating cyclic fragrances, including both natural and synthetic ones, will be discussed, with a focus on the key transformations of alkenes, alkynes, dienes and enynes. Several strategies will be discussed, including cycloaddition, catalytic cyclization, ring-closing metathesis, intramolecular addition, and rearrangement reactions. Representative examples and the featured olfactory investigations will be highlighted, along with some perspectives on future developments in this area.

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Section: Synthesis Of Fragrances Via Rearrangement or Isomerizationmentioning

confidence: 99%

Synthesis of Cyclic Fragrances via Transformations of Alkenes, Alkynes and Enynes: Strategies and Recent Progress

Lin¹,

Huang²,

Ouyang³

et al. 2022

Molecules

View full text Add to dashboard Cite

show abstract

Selective Wacker type oxidation of a macrocyclic diene to the corresponding monounsaturated ketone used as fragrance

Abstract: A selective reaction method for the efficient conversion of an isomeric mixture of 1,9-cyclohexadecadiene (1,9-CHDD) to the corresponding monounsaturated cyclohexadec-8-en-1-one (8-CHD) is described.

Cited by 1 publication

References 42 publications

Synthesis of Cyclic Fragrances via Transformations of Alkenes, Alkynes and Enynes: Strategies and Recent Progress

Synthesis of Cyclic Fragrances via Transformations of Alkenes, Alkynes and Enynes: Strategies and Recent Progress

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