3 years ago

Copper(II) triflate catalyzed regioselective and enantioselective propargylation of Isatin derivatives using Allenylboronic acid pinacol ester

Ajay Jakhar, Mohz Nazish, Noor-ul H. Khan, Rajkumar Tak, Rukhsana I. Kureshy, NAVEEN GUPTA
Abstract: We report a simple protocol for the synthesis of homopropargyl alcohols with isatin derivatives under milder conditions for the first time. The excellent regioselectivity and yields were observed using copper triflate as a Lewis acid catalyst and allenylboronic acid pinacol ester as a nucleophile in aqueous media. The gram level synthesis was done to check the efficiency of the protocol with retention in selectivity. Further one-step functionalization of these homopropargyl alcohols were established as the synthetic application of these alkynes. The enantioselective synthesis of these chiral propargyl alcohols also been explored for the first time with an enantiomeric ratio up to 12:88.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/ejoc.201701745

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