Asymmetric induction mediated by an N–N chiral axis

RS Atkinson, PJ Edwards, GA Thomson

Index: Atkinson, Robert S.; Edwards, Paul J.; Thomson, Gordon A. Journal of the Chemical Society, Chemical Communications, 1992 , # 17 p. 1256 - 1257

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Citation Number: 2

Abstract

Reaction of 3-methylpentane-,-dione with-acetoxyaminoquinazolinone gives an isolable enol, which is chiral by virtue of the high barrier to rotation around its N–N bond; protonation of the double bond occurs in glacial acetic acid to give a single diastereoisomer of keto- amide.

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