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Synthesis and preliminary use of naphthyl quinazoline and isoquinoline oxazolines for asymmetric allylic oxidation
Author(s) -
Andrus Merritt B.,
Sekhar B. B. V. Soma
Publication year - 2001
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570380605
Subject(s) - isoquinoline , chemistry , oxazoline , allylic rearrangement , allylic alcohol , enantioselective synthesis , gratitude , quinazoline , catalysis , stereochemistry , medicinal chemistry , organic chemistry , psychology , social psychology
This paper is dedicated to Professor Jerald S. Bradshaw, undergraduate mentor of MBA, with warmth and gratitude for his encouragement and outstanding leadership. Four new oxazoline ligands, 4‐naphthyl‐2‐phenylquinazoline 4 and 1‐naphthylisoquinoline 5 were made using Suzuki coupling, a Pictet‐Gams reaction, and S ‐amino alcohol. Preliminary use as ligands for asymmetric copper catalyzed allylic oxidation with cyclohex‐ene and perester showed promise providing S ‐cyclohexenyl benzoate product in moderate enantioselectivity (64%ee).