Tetrahedron Letters p. 5689 - 5692 (1998)
Update date:2022-08-02
Topics:
Takeuchi, Kumiko
Kohn, Todd J.
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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