Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
Control of Enantiofacial Differentiation in the Addition Reaction of Organometallics to a Nitrone in the Presence of an External Chiral Auxiliary
Yutaka UkajiTakahiro HatanakaAlauddin AhmedKatsuhiko Inomata
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1993 Volume 22 Issue 8 Pages 1313-1316

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Abstract

It was observed that differentiation of enantiotopic face in the addition reaction of organometallics to 3,4-dihydroisoquinoline N-oxide was well-regulated by the use of an external chiral auxiliary; i.e., Grignard reagents added from the si-face of the nitrone in the presence of bromomagnesium (2S,3R)-4-dimethylamino-1,2-diphenyl-3-methyl-2-butoxide, while dialkylzinc attacked from the re-face.

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© 1993 The Chemical Society of Japan
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