SYNTHESIS OF ALKENES BY REDUCTIVE ELIMINATION OF BETA-HYDROXYSULFOXIMINES

β-Hydroxysulfoximines, obtained in high yield by the addition of α-lithio derivatives of S-alkyl-N-methyl-S-phenyl-sulfoximincs to aldehydes and ketones, undergo reductive elimination to yield alkenes upon treatment with aluminum amalgam in a mixture of tetrahvdrofuran, water, and acetic acid. Dienes and trienes were obtained from enones and dienones. respectively. Diastereomers of 5-(N-methylphenylsuifonimidoyl)-4-octanol were prepared in stereochemically pure forms; reductive elimination of each diastereomer gave rise to a mixture of cis- and trans-4-oclene (60-84% trans). β-Hydroxy sulfides, sulfoxides, and sulfones do not eliminate under comparable conditions. A 1,3 elimination did not occur when 3-(N-methyl-phenylsulfonimidoyl)-1-phenyl-1-propanol was treated with aluminum amalgam: the reaction gave 1-phenyl-1-propanol. © 1979, American Chemical Society. All rights reserved.