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Gold‐Catalyzed Stereoselective Domino Cyclization/Alkynylation of N ‐Propargylcarboxamides with Benziodoxole Reagents for the Synthesis of Alkynyloxazolines
Author(s) -
Zhao Ximei,
Tian Bing,
Yang Yangyang,
Si Xiaojia,
Mulks Florian F.,
Rudolph Matthias,
Rominger Frank,
Hashmi A. Stephen K.
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900264
Subject(s) - stereoselectivity , chemistry , domino , alkynylation , reagent , combinatorial chemistry , catalysis , substrate (aquarium) , cascade , selectivity , cascade reaction , kinetic resolution , stereochemistry , enantioselective synthesis , organic chemistry , oceanography , chromatography , geology
Abstract A concise and highly stereoselective synthesis of alkynyloxazolines via a gold‐catalyzed domino cyclization‐alkynylation cascade of N ‐propargylcarboxamides with benziodoxole reagents is reported. This new protocol, which represents an attractive alternative to two step sequences based on Sonagashira couplings, offers a broad substrate scope, excellent functional group tolerance, and perfect stereoselectivity. A comparison of the computed energies of the isomers of the product suggests kinetic control as the cause of the observed selectivity.