Synthesis and oxidation reactions of cycloheptatrienyl sulfones

✍ Scribed by Zhiwei Tong; Yuzhong Chen; Martin F Hentemann; Philip L Fuchs

• Book ID: 104210937
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 104 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)01386-1

✦ Synopsis

Inexpensive cycloheptatriene is regiospecifically converted to all three phenylsulfonyl substituted cycloheptatrienes. Epoxidation of these materials with achiral reagents is shown to be relatively regiospecific. Reasonable levels of enantiomeric excess ( 63,78%) are achieved by Sharpless asymmetric dihydroxylation of a pair of 3-substituted trienes. Crystallization of these sulfones provides the diols in enantiomeric excesses greater than 90%.