Asymmetric allylsilane-mediated carbocyclization: A highly enantiospecific synthesis of (1S, 2S)-(+)-2-methyl-3-cyclopenten-1-ol
✍ Scribed by Kōichi Mikami; Toshihiko Maeda; Naoyuki Kishi; Takeshi Nakai
- Book ID
- 104233914
- Publisher
- Elsevier Science
- Year
- 1984
- Tongue
- French
- Weight
- 209 KB
- Volume
- 25
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
The asymmetric oxidation of aryl methyl sulfides to sulfoxides with hydroperoxides has been achieved using catalytic amounts of the complex formed in situ between Ti(i-PrO) 4, (S,S)-diphenylethan-l,2-diol 1 and water. The sulfoxides are obtained in 60% yield and 67-80% enantiomeric excess.
Using the quinidine catalyzed cycloaddition reaction of ketene and 2,2dichloroaldehydes, the preparation of several optically pure (S)-methyl-3-hydroxyalkanoates is reported.
An alternate enantiospecific synthesis of methyl (S)-7-tert-butoxycarbonyl-2,3,4,5-tetrahydro-4-methyl-3-oxo-lH-l,4benzodiazepine-2-acetate ( ) is reported. The key step, which involves an intermolecular displacement of the activated aryl fluoride (9) by L-aspartic acid [~-methyl ester, proceeds wit