| Abstract
| - The behavior of (Z)-3-p-tolylsulfinylacrylonitrile (1) as a chiral dienophile has been evaluated fromits reactions with furan and acyclic dienes. Electrostatic interactions of the cyano group with thesulfinyl one restrict the conformational mobility around the C−S bond, thus controlling the π−facialselectivity, which is almost complete in all cases, the approach of the diene from the less-hinderedface of the dienophile (that bearing the lone electron pair) in the predominant rotamer being thefavored one. The regioselectivity is also completely controlled by the cyano group. Additionally,the reactivity of compound 1 as well as its endo-selectivity are both higher than those observed forthe corresponding (Z)-3-sulfinylacrylates, thus proving the potential of sulfinylnitriles as chiraldienophiles.
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