5-Hydroxyproline, Cyclobutane derivatives, Michael addition, Wittig reaction
ARKIVOC - Online Journal of Organic Chemistry 191-2002 (2009)
The synthesis of the 5-hydroxyproline derivatives 3a and 3b using cyclobutane serine analogs 1
and 2 as starting materials is reported. This process occurs with moderate cis/trans selectivity. A
mechanism for this reaction is also proposed. Cyclobutane serine analog 1 was tested in tandem
Michael and Wittig-like reactions, providing some evidence of the mechanism proposed.
This article is dedicated to Professor Benito Alcaide on the occasion of his 60