All articles of this category By treating the anti -hydroxyketones ( 1 and 2 ) and the syn -hydroxyketones ( 4 and 5 ) with samarium(II) iodide, the ketone-olefin coupling cyclizations took place in a stereocontrolled manner to give the trans -decalin diol ( 3 ) and the epimeric mixtures of the cis -decalin diols ( 6 and 7 ) respectively. The observed stereochemistries on the reductive coupling products are established by chelation of the samarium(III) cation generated in the process, with the hydroxyl groups incorporated in the starting materials.
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Kito et al. (1993) studied this question.