A new convenient procedure for the preparation of enantiopure C10-S- and C10-Se-substituted camphor-derived sulfides and selenides
✍ Scribed by Antonio Garcı́a Martı́nez; Enrique Teso Vilar; Amelia Garcı́a Fraile; Santiago de la Moya Cerero; Beatriz Lora Maroto
- Publisher
- Elsevier Science
- Year
- 2001
- Tongue
- French
- Weight
- 93 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The enantiospecific preparation of two novel C10-S(II)-and C10-Se(II)-substituted camphor derivatives (arylsulfide and arylselenide) from readily available camphor is described. The established three-step route constitutes a model procedure for the straightforward preparation of interesting enantiopure C10-S-and C10-Se-substituted camphor-derived chiral sources. The key-step of the described route is an enantiospecific Wagner-Meerwein rearrangement of 3,3-dimethyl-2-methylenenorbornan-1-ol 6 under electrophilic treatment with an arylsulfenyl (or arylselenyl) chloride.