Synthesis and reduction of chiral sulfinyl cyclohexanones

✍ Scribed by M.C. Carreño; J.L.García Ruano; A. Rubio

• Book ID: 104227941
• Publisher: Elsevier Science
• Year: 1987
• Tongue: French
• Weight: 264 KB
• Volume: 28
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)96645-0

✦ Synopsis

The reaction of cyclohexanone with (S)-(-)-menthyl-p-toluenesulfinate in the presence of Pr@gBr yields a mixture of enantiomerically pure 2-p-tolylsulfinylcyclohexanone diastereoisomers. Their stereoselective reduction to chiral hydroxysulfoxides is also reported.

The important role of chiral 8-ketosulfoxides in asymnatric synthesis has been reflected in many papersl. Synthesis of acyclic enanticmerically pure substrates was easily achieved fran CR)-(-j-p-tolylmethylsulfoxide2, nevertheless, cyclic B-ketosulfoxides are not accessible by this way.