Enantiopure Sulfinyl-1,3-dienes as Powerful Partners in Stereoselective Diels—Alder Cycloadditions
✍ Scribed by Maria Chiara Aversa; Anna Barattucci; Paola Bonaccorsi; Placido Giannetto
- Book ID
- 101986757
- Publisher
- John Wiley and Sons
- Year
- 2006
- Weight
- 8 KB
- Volume
- 37
- Category
- Article
- ISSN
- 0931-7597
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📜 SIMILAR VOLUMES
Application of the Stereoselective Diels-Alder Reaction of Enantiopure 2-Sulfinyl Dienes: Synthesis of (-)-(1S,5R)-Karahana Ether. -The natural karahana ether (VII) is synthesized for the first time by application of sulfinyl derivative (I) as chiral auxiliary in asymmetric Diels-Alder reaction and
Enantiopure sulfinylquinones (+)-2 and (+)-3 reacted with Dane's diene 1 under thermal and ZnBr 2 Lewis acid conditions with reversal regiochemistry but similar ~-facial diastereoselectivity to afford, after spontaneous elimination of the sulfinyl group, tetracyclic derivatives 4-9.