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Copper(II) Triflate Catalyzed Regioselective and Enantioselective Propargylation of Isatin Derivatives by Using Allenylboronic Acid Pinacol Ester
Author(s) -
Gupta Naveen,
Tak Rajkumar,
Nazish Mohd,
Jakhar Ajay,
Khan Noorul H.,
Kureshy Rukhsana I.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701745
Subject(s) - chemistry , pinacol , regioselectivity , isatin , enantioselective synthesis , organic chemistry , nucleophile , propargyl , catalysis , trifluoromethanesulfonate , selectivity , combinatorial chemistry
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 with copper triflate as a Lewis‐acid catalyst and allenylboronic acid pinacol ester as a nucleophile in aqueous media. A gram‐scale synthesis was done to check the efficiency of the protocol with retention in selectivity. Further one‐step functionalization of these homopropargyl alcohols was established as the synthetic application of these alkynes. The enantioselective synthesis of these chiral propargyl alcohols has also been explored for the first time with an enantiomeric ratio up to 12:88.