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Proximal heteroalkylation of monoalkoxycalix[4]arenes in synthesis of inherently chiral molecules
- Source :
- Tetrahedron. 65:4220-4227
- Publication Year :
- 2009
- Publisher :
- Elsevier BV, 2009.
-
Abstract
- Proximal heteroalkylation of monoalkyl ethers of calix[4]arenes or p - tert -butylcalix[4]arenes in NaH/CH 3 CN or NaOH/DMSO, respectively, was applied for synthesis of inherently chiral calixarenes with ABHH substitution pattern. The introduction by the method of ( R )- or ( S )- N -(α-phenylethyl)acetamide chiral auxiliary group gives mixtures of diastereomeric derivatives of inherently chiral calixarenes, which were separated by column chromatography. The chiral calixarenes were thoroughly characterized by 1 H, 13 C NMR, and X-ray diffraction methods.
Details
- ISSN :
- 00404020
- Volume :
- 65
- Database :
- OpenAIRE
- Journal :
- Tetrahedron
- Accession number :
- edsair.doi...........88eb3d29e0a35ce11801dc9ab15ab4e2