4th EucheMs chemistry congress

wednesday, 29-Aug 2012
s768
chem. Listy 106, s587–s1425 (2012)
organic Chemistry, Polymers – i
General synthetic methods – iii
o - 3 6 1
reCent deveLoPMentS of new
StereoSeLeCtive MuLtiPLe Bond-forMinG
trAnSforMAtionS
J. rodriGuez 1
1 Aix-Marseille University, Institut des Sciences Moleculaires de
Marseille, Marseille cedex 20, France
The presentation will be devoted to some of our recent
contributions on the utilization of activated carbonyls towards the
development of new MBFTs involving organocatalyzed
asymmetric Michael addition, selective intramolecular trapping
of iminiums and microwave-promoted both olefin metathesis and
acyl-Wolff rearrangement allowing the facile preparation of
polyheterocyclic systems with a high level of complexity and
diversity.
Keywords: Michael addition; Multicomponent Reactions;
Carbanions; Molecular diversity; Synthetic Methods;
General synthetic methods – iii
4 th EucheMs chemistry congress
o - 3 6 2
PrePArAtionS of reGioSeLeCtiveLy
MonoSuBStituted ALPhA-, BetA- And GAMMA-
CyCLodextrin derivAtiveS – PreCurSorS for
further SyntheSiS.
J. JindriCh 1 , M. rezAnKA 1 , M. BLAhovA 1 ,
e. BednArovA 1
1 Faculty of Science Charles University in Prague, Department
of Organic and Nuclear Chemistry, Prague 2, Czech Republic
Alkylation of α-, β- or γ-cyclodextrin with allyl, cinnamyl
or propargyl bromide followed by peracetylation of remaining
hydroxyl groups and separation of isomers resulted in the sets of
peracetylated 2I-O-, 3I-O- and 6I-O-alkylated cyclodextrins.
Ozonolyzis or oxidative cleaveage of peracetylated allyl or
cinnamyl derivatives resulted in complete sets of peracetylated
2I-O-, 3I-O- and 6I-O- formylmethyl or carboxymethyl derivatives
which are, as well as the propargyl derivatives, useful precursors
for preparation of regioselectively monosubstituted derivatives of
cyclodextrins. All compounds were characterized by 2D-NMR
techniques. The carboxymethyl derivatives were used as chiral
selectors in capillary electrophoresis. Substantial differences in
separation abilities among the regioisomers were observed. Thus,
the importance of performing supramolecular interaction
experiments with pure regiosomers of cyclodextrin derivatives
was confirmed.
Keywords: cyclodextrins; synthetic methods; electrophoresis;
NMR spectroscopy; supramolecular chemistry;
AUGUst 26–30, 2012, PrAGUE, cZEcH rEPUbLIc