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Substituent effects in the stereoconvergent synthesis of β-hydroxyphenylalanine derivatives

✍ Scribed by Craig A. Hutton

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
203 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

The degree of stereoconvergence in the synthesis of I~-hydroxyarylalanine derivatives from the corresponding ~-bromoarylalanine derivatives is governed by the electronic nature of the aryl substituents, and controlled by facially selective stabilisation of the benzylic cation through the neighbouring ester moiety. Introduction of electron donating aryl substituents results in a decrease in selectivity, whereas electron withdrawing substituents induce an increase in selectivity for the

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