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Diastereoselection in the nucleophilic conjugate addition of amines to 2-hydroxyalkylpropenoates

✍ Scribed by P. Perlmutter; M. Tabone

Publisher: Elsevier Science
Year: 1988
Tongue: French
Weight: 192 KB
Volume: 29
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)82490-9

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✦ Synopsis

Nucleophilic conjugate addition of benzylamine to 2-hydroxyalkylpropenoates la-c proceeds in high yield with modest diastereoselection. However, addition of benxylamine to the silyl ether of lc produces only the anti-isomer 2d in high yield Although nucleophilic conjugate additions of amines to 2-substituted propenoates have occasionally been reported2 little attention has been paid to such additions to propenoates bearing a chiral substituent at C2,

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