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

作者：Christensen Jannie; Albrecht Lukasz; Jorgensen Karl Anker^*

来源：Chemistry-An Asian Journal, 2013, 8(3): 648-652.

DOI：10.1002/asia.201201072

• asymmetric synthesis
• cyclization
• dihydrobenzofurans
• Michael addition
• organocatalysis

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.

• 出版日期2013-3