Chiral trialkanolamine-based hemicryptophanes: synthesis and oxovanadium complex.
[reaction: see text] A novel class of chiral hemicryptophane hosts has been synthesized in diastereoisomerically pure form, namely, M-(R,R,R)-1a/P-(S,S,S)-1a and M-(S,S,S)-1b/P-(R,R,R)-1b. The C3-symmetrical precursor 9 was prepared, using either (R)- or (S)-glycidyl nosylate, repectively, as the chiral pool reactant and subsequently cyclized (trimerized) in the presence of Sc(OTf)3. The four stereoisomers were fully characterized and displayed two pairs of mirror-image CD spectra, which were used to determine their absolute configuration. The formation of the oxovanadium(V) complex of hemicryptophane 1a is also reported.
Gautier
Arnaud
A
Laboratoire de Chimie, Ecole Normale Supérieure de Lyon, UMR CNRS 5182, 46, Allée d'Italie, F-69364 Lyon 07, France.
Mulatier
Jean-Christophe
JC
Crassous
Jeanne
J
Dutasta
Jean-Pierre
JP