Rh(II)-Catalyzed Cyclopropanation of Furans and Its Application to the Total Synthesis of Natural Product Derivatives

Verena Lehner; Huw M L Davies; Oliver Reiser

doi:10.1021/acs.orglett.7b02009

Rh(II)-Catalyzed Cyclopropanation of Furans and Its Application to the Total Synthesis of Natural Product Derivatives

Org Lett. 2017 Sep 15;19(18):4722-4725. doi: 10.1021/acs.orglett.7b02009. Epub 2017 Aug 28.

Authors

Verena Lehner^{1

2}, Huw M L Davies², Oliver Reiser¹

Affiliations

¹ Institute of Organic Chemistry, University of Regensburg , Universitätsstraße 31, 93053 Regensburg, Germany.
² Department of Chemistry, Emory University , 1515 Dickey Drive, Atlanta, Georgia 30322, United States.

PMID: 28846420
DOI: 10.1021/acs.orglett.7b02009

Abstract

Rh(II)-catalyzed enantioselective cyclopropanations of furans, providing access to synthetically useful building blocks, are reported. After screening of 10 Rh(II) catalysts, Rh₂(S-TCPTTL)₄ was identified as a highly efficient and selective catalyst (up to 98% ee, TON 88000, and TOF 24/s) for the cyclopropanation of furans. These cyclopropanes were successfully applied to the enantioselective synthesis of novel paraconic acid derivatives.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.
Research Support, Non-U.S. Gov't