Copper(II) Triflate Catalyzed Regioselective and Enantioselective Propargylation of Isatin Derivatives by Using Allenylboronic Acid Pinacol Ester

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...

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Bibliographic Details
Published in:European journal of organic chemistry 2018-03, Vol.2018 (11), p.1384-1392
Main Authors: Gupta, Naveen, Tak, Rajkumar, Nazish, Mohd, Jakhar, Ajay, Khan, Noor‐ul H., Kureshy, Rukhsana I.
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
Alkynes
Allenes
Allenylboronic acid
Copper
Copper compounds
Derivatives
Homopropargyl alcohol
Isatin
Regioselectivity
Synthesis
Synthetic methods
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Summary: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. Regioselective propargylation of isatins in aqueous media. With this protocol we could achieve propargyl alcohols in high yields with wide substrate scope. The enantioselective version was also explored to yield chiral alcohols with er up to 12:88, which is reported for the first time.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201701745