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

✍ Scribed by Merritt B. Andrus; B. B. V. Soma Sekhar

Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
89 KB
Volume
38
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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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