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A Tripodal Peptidic Titanium Phosphonate as a Homochiral Porous Solid Medium for the Heterogeneous Enantioselective Hydration of Epoxides
Author(s) -
Milo Anat,
Neumann Ronny
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000373
Subject(s) - chemistry , enantioselective synthesis , phosphonate , titanium , polymer chemistry , lamellar structure , polymerization , organic chemistry , crystallography , polymer , catalysis
A porous, homochiral titanium‐phosphonate material based on a tripodal peptide scaffold was used as a heterogeneous reaction medium for the enantioselective hydration (>99%) of styrene oxide. This titanium‐phosphonate material, which was shown to contain confined chiral spaces, was prepared by polymerization of L ‐leucine onto a tris(2‐aminoethyl)amine initiator, followed by capping with phosphonate groups and completed by non‐aqueous condensation with titanium isopropoxide. Circular dichroism confirmed that the peptide tethers yielded a secondary structure. X‐ray powder diffraction and transmission electron microscopy supported by a semi‐empirical model showed the likely formation of a porous, lamellar material that was quantified by nitrogen adsorption.