Asymmetric Diels-Alder reaction: Cis-1-arylsulfonamido-2-indanols as highly effective chiral auxiliaries
β Scribed by Arun K. Ghosh; Packiarajan Mathivanan
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- English
- Weight
- 236 KB
- Volume
- 7
- Category
- Article
- ISSN
- 0957-4166
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β¦ Synopsis
Lewis acid promoted Diels-Alder reaction of acrylate esters of -1-arylsulfonamido-2-indanols and cyclopentadiene provided exclusively -adducts with high -diastereoselectivities.
π SIMILAR VOLUMES
The use ofa mono-pivalate mono-acrylate bis-ester of (+)-lS,5S,6S-spirol4.4]nonane-l,6diol in an asymmetric Dieis-Alder reaction with cyclopentadiene (2 equiv. BCI3, -85Β°C, CH2C12) provided the expected endo bicyclo adduct in >97% de. Iodolactonization of the bicyclo adduct provided the (+)-lactune
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