Enantioselective Route to Ketones and Lactones from Exocyclic Allylic Alcohols via Metal and Enzyme Catalysis

Warner, Madeleine C.Stockholms universitet,Institutionen för organisk kemi (author)

AuthorCount:4;
A general and efficient route for the synthesis of enantiomerically pure a-substituted ketones and the corresponding lactones has been developed. Ruthenium- and enzyme-catalyzed dynamic kinetic resolution (DKR) with a subsequent Cu-catalyzed alpha-allylic substitution are the key steps of the route. The a-substituted ketones were obtained in high yields and with excellent enantiomeric excess. The methodology was applied to the synthesis of a naturally occurring caprolactone, (R)-10-methyl-6-undecanolide, via a subsequent Baeyer-Villiger oxidation.

Nagendiran, AnujaStockholms universitet,Institutionen för organisk kemi(Swepub:su)anna4649 (author)
Bogár, KrisztiánStockholms universitet,Institutionen för organisk kemi (author)
Bäckvall, Jan-E.Stockholms universitet,Institutionen för organisk kemi(Swepub:su)backv (author)
Stockholms universitetInstitutionen för organisk kemi (creator_code:org_t)

In:Organic Letters: American Chemical Society (ACS)14:19, s. 5094-50971523-70601523-7052

By the author/editor: Warner, Madelein ...; Nagendiran, Anuj ...; Bogár, Krisztián; Bäckvall, Jan-E.

About the subject

NATURAL SCIENCES: NATURAL SCIENCES; and Chemical Science ...; and Organic Chemistr ...

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