Stereoselectivity in the Wittig reaction of phenyl 3-pyridyl ketones: Amide substituent effect on the preferential (E)-ollefin formation
K Takeuchi, TJ Kohn
Index: Takeuchi, Kumiko; Kohn, Todd J. Tetrahedron Letters, 1998 , vol. 39, # 32 p. 5689 - 5692
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Citation Number: 4
Abstract
A Wittig reaction of amide substituted phenyl 3-pyridyl ketones with “nonstabilized” phosphorus ylides which contain a carboxyl terminus preferentially forms (E)-olefin. The preference for this stereoselectivity stems from either hydrogen bonding or salt-bridge formation between the amide group and the carboxyl terminus during the oxaphosphetane intermediate formation.
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[Takeuchi, Kumiko; Kohn, Todd J.; True, Timothy A.; Mais, Dale E.; Wikel, James H.; Utterback, Barbara G.; Wyss, Virginia L.; Jakubowski, Joseph A. Journal of Medicinal Chemistry, 1998 , vol. 41, # 27 p. 5362 - 5374]
[Takeuchi, Kumiko; Kohn, Todd J.; True, Timothy A.; Mais, Dale E.; Wikel, James H.; Utterback, Barbara G.; Wyss, Virginia L.; Jakubowski, Joseph A. Journal of Medicinal Chemistry, 1998 , vol. 41, # 27 p. 5362 - 5374]
[Takeuchi, Kumiko; Kohn, Todd J.; True, Timothy A.; Mais, Dale E.; Wikel, James H.; Utterback, Barbara G.; Wyss, Virginia L.; Jakubowski, Joseph A. Journal of Medicinal Chemistry, 1998 , vol. 41, # 27 p. 5362 - 5374]