Synthesis and preliminary use of naphthyl quinazoline and isoquinoline oxazolines for asymmetric allylic oxidation | Zendy

Andrus Merritt B. | Zendy; Sekhar B. B. V. Soma | Zendy

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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).

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