ChemInform Abstract: Highly Diastereoselective Intermolecular β-Addition of Alkyl Radicals to Chiral 2-(Arylsulfinyl)-2-cycloalkenones.

✍ Scribed by N. MASE; Y. WATANABE; Y. UENO; T. TORU

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 43 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199814078

✦ Synopsis

Highly Diastereoselective Intermolecular β-Addition of Alkyl Radicals to Chiral 2-(Arylsulfinyl)-2-cycloalkenones.

-The reaction of cycloalkenones having chiral bulky arylsulfinyl groups proceeds with excellent diastereoselectivity. In the presence of the Lewis acids EtAlCl 2 and TiCl 2 (OiPr) 2 reversed diastereoselectivity is observed, while addition of ZnBr 2 , MgCl 2 , or ZrCl 4 leads to small change in diastereoselectivity. Since the sulfinyl group can easily be removed, these reactions provide an effective route to chiral 3-alkylcyclopentanones and -cyclohexanones. -(MASE, N.; WATANABE,