Syntheses and Odor Descriptions of Cyclopropanated Compounds. Part 5

Synthesis of both enantiomers of methyl 4,5-didehydrojasmonate (1, D 4,5 -MJA; > 99.8% ee), a constituent of jasmin absolute, established the absolute configuration of the natural product, and their odor quality was evaluated. The fragrance of the natural (3S,7R)-enantiomer (a fresh natural, sweet floral fruity odor, reminiscent of Jasmin and Ylang Ylang flower, more intensive and tenacious) was superior to that of the unnatural (3R,7S)-enantiomer (a floral green odor with slight metallic green aspect, less intensive than the natural form) and the racemate (green-floral note, having weak and less volume than methyl jasmonate). Odor difference between natural and unnatural enantiomers of methyl jasmonate (2) is also reported.

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Present and Future of Cyclopropanations in Fragrance Chemistry

Schröder¹

2014

Chemistry & Biodiversity

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The elaboration of new cyclopropanation methods is expected to make selectively new Δ-compounds available, either as precursors or as new ingredients with superior olfactory impacts. The improvement of cyclopropanation processes through understanding of reaction mechanisms reduces costs and environmental impact. Givaudan is the leading 'Flavor & Frangrance' company which successfully brings Δ-molecules to the market. Javanol(®) , for example, with its unique performance exemplifies the product of an efficient industrial cyclopropanation of a dienol precursor. Serenolide(®) , Toscanol(®) , and Pashminol(®) are other high-impact Δ-fragrance ingredients manufactured at Givaudan. This review describes our journey from advanced SimmonsSmith methodology using Zn carbenoids, to Al- and Mg-mediated cyclopropanation techniques in the context of related alternative cyclopropanation methods for the transfer of the CH2 group onto CC bonds. The resulting cyclopropane products are themselves interesting substrates for further transformation to other flavor and fragrance compounds. Throughout this Review, the notation Δ refers to the presence of a cyclopropane ring, i.e., a 'Δ-compound' is defined as a compound that contains a cyclopropyl substituent or a 'fused cyclopropa' component, or a 'spiro-cyclopropane' moiety.

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Syntheses and Odor Descriptions of Cyclopropanated Compounds. Part 5

Cited by 10 publications

References 20 publications

Syntheses and Odor Descriptions of Cyclopropanated Compounds, Part 6

Syntheses and Odor Descriptions of Cyclopropanated Compounds, Part 6

Synthesis and Odor Description of Both Enantiomers of Methyl 4,5-Didehydrojasmonate, a Component of Jasmin Absolute

Present and Future of Cyclopropanations in Fragrance Chemistry

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