ChemInform Abstract: Synthesis and Characterization of Optically Active Spiro[4.5]decanes.

✍ Scribed by Sara Rafel; Gemma Cabarrocas; Montserrat Ventura; Teo Parella

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 33 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199916039

✦ Synopsis

Synthesis and Characterization of Optically Active Spiro[4.5]decanes. -Three different dienes (I), substituted with a chiral auxiliary at the 1-position, and dienophiles (II) or (VII) undergo a Diels-Alder cycloaddition with quite good diastereofacial selectivity. The Si-exo and Re-endo diastereomers (III)/(VIII) and (IV)/(IX) respectively are the most favored ones. The bulky acetoxy group in dienophile (VII) has little effect on the diastereofacial selectivity. The use of Lewis acids as catalysts to enhance selectivity is been attempted without success. -(RAFEL, SARA; CABARROCAS, GEMMA;