Enantioselective [4 + 2]-Annulation of Oxadienes and Allenones Catalyzed by an Amino Acid Derived Phosphine: Synthesis of Functionalized Dihydropyrans.

Org Lett

Graduate School for Integrative Sciences & Engineering (NGS), Centre for Life Sciences (CeLS), National University of Singapore, #05-01, 28 Medical Drive, Singapore 117456 Singapore.

Published: May 2016

An enantioselective [4 + 2]-annulation process between cyano-activated oxadienes and allenones is developed. An l-valine-derived phosphine was efficient in catalyzing the reaction, and a wide range of highly functionalized dihydropyrans were prepared in high yields and with excellent enantioselectivities.

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http://dx.doi.org/10.1021/acs.orglett.6b00760DOI Listing

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