Highly Z-selective asymmetric 1,4-addition reaction of 5H-oxazol-4-ones with alkynyl carbonyl compounds catalyzed by chiral guanidines.
J Am Chem Soc
; 133(15): 5695-7, 2011 Apr 20.
Article
em En
| MEDLINE
| ID: mdl-21449589
ABSTRACT
An asymmetric 1,4-addition reaction of 5H-oxazol-4-ones with alkynyl carbonyl compounds was developed, and, for the first time, high enantiomeric and geometric control was achieved to afford the thermodynamically unstable Z-isomer predominantly using chiral guanidine catalysts bearing a hydroxy group at the appropriate position. The method provides synthetically useful γ-butenolide ester bearing a chiral quaternary stereogenic center.
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MEDLINE
Idioma:
En
Ano de publicação:
2011
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Article