Tetrahedron p. 1991 - 1999 (1983)
Update date:2022-09-26
Topics:
Meyers, A. I.
Hanagan, Mary Ann
Trefonas, L. M.
Baker, R. J.
Chiral aromatic oxazolines were prepared for utilization in asymmetric C-C bonding reactions.Lithiation of aryloxazolines could not be accomplished directly but were efficiently lithiated via halogen metal exchange of the o-bromo derivative (16).The resulting lithio compound (9) reacted smoothly with carbonyls to give adducts 19 but with poor stereoselectivity.Hydrolysis gave the phthalides 4 in poor ee's (20-25percent).When the lithio-oxazolines 9 were transformed into 21, they now served as chiral electrophiles.Addition of organometallics to 21 gave, particularly with Grignard reagents, useful levels of asymmetric induction which, after hydrolysis, gave phthalides 4 in 40-80percent ee.
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Doi:10.1016/S0040-4039(00)88585-8
(1982)Doi:10.1055/s-1982-30016
(1982)Doi:10.1002/anie.201002889
(2010)Doi:10.1021/jo00151a025
(1983)Doi:10.1039/c39820000943
(1982)Doi:10.1016/S0040-4039(00)85223-5
(1986)