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Rhodium‐Catalyzed Regioselective Domino Azlactone–Alkyne Coupling/Aza‐Cope Rearrangement: Facile Access to 2‐Allyl‐3‐oxazolin‐5‐ones and Trisubstituted Pyridines
Author(s) -
Kuang Jinqiang,
Parveen Shaista,
Breit Bernhard
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201704022
Subject(s) - regioselectivity , rhodium , domino , alkyne , chemistry , catalysis , combinatorial chemistry , atom economy , medicinal chemistry , organic chemistry
Rhodium‐catalyzed regioselective addition of azlactones to internal alkynes combined with aza‐Cope rearrangement provides efficient atom economic access to 2‐allyl‐3‐oxazolin‐5‐one derivatives. Extension to a triple domino process, in which the above process is combined with in situ azlactone formation starting from amino acids renders this process even more attractive. Subsequent thermolysis of the 2‐allyl‐3‐oxazolines enabled the de novo synthesis of trisubstituted pyridines.