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Cyclobutane serine amino acid derivatives as 5-hydroxyproline precursors

AuthorsPérez-Fernández, Marta; Avenoza, Alberto; Busto, Jesús H.; Peregrina, Jesús M.; Rodríguez, Fernando
Cyclobutane derivatives
Michael addition
Wittig reaction
Issue Date10-Jun-2009
CitationARKIVOC - Online Journal of Organic Chemistry 191-2002 (2009)
AbstractThe 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.
DescriptionThis article is dedicated to Professor Benito Alcaide on the occasion of his 60 th birthday
Publisher version (URL)http://www.arkat-usa.org/arkivoc-journal/browse-arkivoc/2010/3/
Appears in Collections:(ICVV) Artículos
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