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Karl Anker Jørgensen

Stereocontrolled Organocatalytic Strategy for the Synthesis of Optically Active 2,3-Disubstituted cis-2,3-Dihydrobenzofurans

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An intramolecular, organocatalyzed Michael addition has been developed to obtain biologically important 2,3-disubstituted cis-2,3-dihydrobenzofurans. By using mandelic acid salts of primary aminocatalysts, derived from cinchona alkaloids, the intramolecular cyclization reaction has been developed to proceed in high yield, with moderate to good diastereoselectivity, and up to 99 % ee. Based on the absolute configuration of the formed 2,3-disubstituted-cis-2,3- dihydrobenzofurans and by considering the observed substrate scope restrictions, a mechanistic rationalization has been presented. An intramolecular, organocatalyzed Michael addition to obtain biologically important 2,3-disubstituted cis-2,3-dihydrobenzofurans has been developed. By using mandelic acid salts of primary aminocatalysts, derived from cinchona alkaloids, the intramolecular cyclization reaction proceeded in high yield, with moderate to good diastereoselectivity, and up to 99 % ee.
Original languageEnglish
JournalChemistry - An Asian Journal
Volume8
Issue3
Pages (from-to)648-652
Number of pages5
ISSN1861-4728
DOIs
Publication statusPublished - 2013

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