Enantioselective Sulfoxidation and Kinetic Resolution Combined Protocol Mediated by a Functionalized (S)-Norcamphor-Based Hydroperoxide/Titanium(IV) Isopropoxide System

✍ Scribed by Alessandra Lattanzi; Sandro Piccirillo; Arrigo Scettri

• Publisher: John Wiley and Sons
• Year: 2007
• Tongue: English
• Weight: 118 KB
• Volume: 349
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/adsc.200600267

✦ Synopsis

Abstract

A functionalized tertiary furyl hydroperoxide derived from (S)‐norcamphor has been easily synthesized in good yield and in a highly diastereoselective manner. Good to high enantioselectivities (up to 99 % ee) and acceptable to good yields (up to 86 %) were achieved for the sulfoxides, by tandem stereoconvergent asymmetric sulfoxidation and kinetic resolution when using the novel hydroperoxide as oxygen donor and chirality source in the presence of catalytic loadings of titanium(IV) isopropoxide as the catalyst.