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Sequential Au/Cu Catalysis: A Two Catalyst One‐Pot Protocol for the Enantioselective Synthesis of Oxazole α‐Hydroxy Esters via Intramolecular Cyclization/Intermolecular Alder‐Ene Reaction
Author(s) -
Nalivela Kumara Swamy,
Rudolph Matthias,
Baeissa Elham S.,
Alhogbi Basma G.,
Mkhalid Ibraheem A. I.,
Hashmi A. Stephen K.
Publication year - 2018
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.201800246
Subject(s) - oxazole , chemistry , enantioselective synthesis , intramolecular force , catalysis , intermolecular force , ene reaction , yield (engineering) , combinatorial chemistry , stereochemistry , organic chemistry , molecule , materials science , metallurgy
A convenient protocol for the enantioselective synthesis of oxazole α‐hydroxy ester derivatives 4 from readily available propargylamides 1 and alkylglyoxylates 3 was developed. The first step of the one‐pot procedure is the selective intramolecular in situ formation of an alkylideneoxazoline 2 , which then in an intermolecular reaction is enantioselectively transformed to the oxazole α‐hydroxy ester derivatives 4 in quantitative yield and good to excellent enantioselectivity via an asymmetric copper(II)‐catalyzed Alder‐ene reaction.