Asymmetric Oxyselenenylation of Olefins Using Optically Active Selenobinaphthyls and d-Menthol as a Nucleophile

Article abstract of DOI:10.1246/cl.1992.1123

In order to improve the diastereomeric excess (d.e.) in asymmetric oxyselenenylation of symmetrical cis-olefins using bis <(R)-(2'-acetylamino-1,1'-binaphthalene)-2-yl> diselenide, the use of d- and l-menthol was examined as nucleophiles.The d.e. was further enhanced for symmetrical cis-olefins as well as trans-β-methylstyrene by using d-menthol due to double stereodifferentiation between the (R)-binaphthyl and d-menthol.