Synthesis of chiral crownophanes via tandem Claisen rearrangement
โ Scribed by Hideo Tokuhisa; Yoshinobu Nagawa; Hirotaka Uzawa; Kazuhisa Hiratani
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 245 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
A synthetic route for crownophanes containing a chiral binaphthyl unit using tandem Claisen rearrangement is described to demonstrate the versatility of this approach. Molecular recognition by the resulting crownophane for butylurea is also investigated.
๐ SIMILAR VOLUMES
Bis(naphthyl)crownophanes having an isobutenyl group and different ring size were synthesized. By control of the reaction temperature and time, both the first-step product having one hydroxyl group and the second-step product having two hydroxy groups can be isolated in high yields.
A variety of a-C-glycosides may be accessed in an entirely stereoselective fashion from 3-OH glycal esters, by way of the tandem reaction sequence of Tebbe methylenation and Claisen rearrangement. In contrast with previous studies in the corresponding b-series, careful control of conditions for Clai