Stereocontrolled reactions mediated by remote sulfoxides: Formation and reactivity of enantiomerically pure benzylic centers

✍ Scribed by José Luis García Ruano; Ana M. Martín Castro

• Publisher: John Wiley and Sons
• Year: 2007
• Tongue: English
• Weight: 704 KB
• Volume: 18
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.20342

✦ Synopsis

Abstract

Reactions of different electrophiles (alkyl halides, aldehydes, N‐sulfinylimines, imines, etc) with (S)‐2‐p‐toluenesulfinyl toluene and their alkyl, triisopropylsilyloxy, and methylthio derivatives at benzylic position, in the presence of LDA, allow the synthesis of a variety of enantiomerically pure benzylic centers, whose configuration is efficiently controlled by the γ‐sulfinyl group, according to 1,4‐asymmetric induction processes. With prochiral electrophiles, the 1,5‐asymmetric induction processes can also be controlled either by modifying their steric or electronic features or by incorporating an additional chiral center at the electrophiles. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:537–548, 2007; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20342