Organic Letters
Letter
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In summary, we have described a convenient way to synthesize
enantiopure hemicryptophane hosts involving a reductive
amination between a chiral enantiopure tren moiety and a
racemic CTV derivative. A thermodynamic resolution was
observed: only the M-SSS diasteromeric cage compound was
obtained allowing for an easy purification of the product. We can
also notice that this corresponds to a remarkable remote
stereocontrol of the chirality of the CTV unit by the stereogenic
centers of the tren moiety because it was achieved through 10
covalent bonds (10 Å) whatever the nature of the substituents on
the tren’s asymmetric carbons. This constitutes an important
step in the development of enantiopure hemicryptophane
derivatives as chiral sensors or catalysts.
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́
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ASSOCIATED CONTENT
* Supporting Information
■
S
Synthetic procedures; NMR spectra; experimental and calculated
ECD spectra; computational methods; X-ray data for MSSS-5a.
This material is available free of charge via the Internet at http://
AUTHOR INFORMATION
Corresponding Author
■
Notes
The authors declare no competing financial interest.
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