Sulfoxides in radical chemistry. High 1,2-asymmetric induction in radical cyclizations

✍ Scribed by Christoph Imboden; Thierry Bourquard; Olivier Corminboeuf; Philippe Renaud; Kurt Schenk; Mohamed Zahouily

• Book ID: 104260441
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 257 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)02420-4

✦ Synopsis

Very high levels of 1,2-asymmetric induction (>50:1) from the sulfur chiral center are reached for the cyclization of substituted l-(ortho-chlorophenyl)sulfinyl-5-hexen-1-yl radicals. These reactions represent the first cases of high asymmetric 1,2-induction during cyclizations of non-stabilized sulfinylated alkyl radicals. They open promising perspectives for the synthesis of enantiomerically pure cyclic and polycyclic derivatives.