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Stereochemical outcome of reactions involving 1,1-bis(seleno) 4-tert-butyl cyclohexanes

✍ Scribed by Alain Krief; Elie Badaoui; Willy Dumont; Laszlo Hevesi; Bernard Hennans; Reiner Dieden

Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
322 KB
Volume
32
Category
Article
ISSN
0040-4039

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✦ Synopsis

Stereoselective allylation of conformationally rigid 4-tert-butyl-I,l-bis(methylseleno) cyclohexanes I has been achieved @from the axial face on sequential reaction of I with alkyllithiums, copper iodide-dimethyl su&ie and ally1 bromides and (ii)fiom the equatorial face on reaction with ally1 stannanes or -silanes in the presence of a Lewis acid. The synthesis of 1 -selenocyclohexane has been

achieved from I via the "carbanionic ronte" or with tin hydride through a "radical route". The former reaction lea& selectively to the trans selenides whereas both stereoisomers are produced in the latter process.

πŸ“œ SIMILAR VOLUMES

Stereoselective synthesis and reactions
Stereoselective synthesis and reactions of 1-seleno-4-tert-butyl cyclohexyllithiums
✍ A. Krief; G. Evrard; E. Badaoui; V. De Beys; R. Dieden πŸ“‚ Article πŸ“… 1989 πŸ› Elsevier Science 🌐 French βš– 293 KB

The axial C-Se bond of seleno-and mixed selenoacetak derivedfrom I-tert-butyl cyc2ohexanones exhibit a high tendency to be cleaved by n-butyllithium. The resulting 1 -selerw+tert-butyl cyclohexyllithium are selective& protonated or seIenyIated via axial attack. We recently described 1 that l,l-bis@