Dancing around the expense of multi-step biocatalyst reactions? The inventors on this patent application describe a sweet-smelling, one-step, commercially viable solution.
One-step synthesis of chirally enriched, flowery 2,4-disubstituted tetrahydropyran-4-ol
WIPO Patent Application WO/2016/059648
Publication date: April 21, 2016
Assignee: S.H. Kelkar And Company Ltd.
This invention describes a single-step process for synthesizing chirally enriched 2,4-disubstituted tetrahydropyran-4-ol and its derivatives. It does so using an organocatalyst that is less expensive, making the process commercially viable. The resulting materials exhibit fresh, soft, sweet and natural floral odors reminiscent of muguet, with some rose oxide side notes and earthy nuances resembling natural odors.
Previously described processes employ multiple steps and biocatalysts during reactions, in the end yielding less of the final product. These biocatalysts can be expensive and make the process commercially unviable.
The disclosed process comprises the asymmetric reaction of an aliphatic aldehyde and a homoallylic alcohol in the presence of a chiral organocatalyst. The chirally enriched 2,4-disubstituted tetrahydropyran-4-ol and its derivatives produced can create finished products that are already enantiomerically and/or diasteriomerically pure, or at least substantially enriched in the desired chiral molecules.
Furthermore, the chirally enriched compounds exhibit increased bioactivity intensity, which results in a corresponding increase in persistence of the aroma given off by the perfumery composition. Therefore less concentration of the odorant is required to provide a lasting aroma, compared with conventional perfumery compositions. For more information, see the patent application.
Patent application accessed May 13, 2016.