212309-40-5Relevant academic research and scientific papers
Stereoselectivity in the Wittig reaction of phenyl 3-pyridyl ketones: Amide substituent effect on the preferential (E)-olefin formation
Takeuchi, Kumiko,Kohn, Todd J.
, p. 5689 - 5692 (1998)
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.
