RESUMO
Kinetic resolution of racemic C-3 substituted pyrrolidine-2,5-diones has been achieved for the first time using highly efficient oxazaborolidine catalysts derived from cis-1-amino-indan-2-ol.
Assuntos
Compostos Aza/química , Compostos de Boro/química , Succinimidas/química , Catálise , Indanos/química , Cinética , Estereoisomerismo , Succinimidas/isolamento & purificaçãoRESUMO
Reactions and purifications, including carbon-carbon bond forming reactions, can be carried out on a cellulose support on which the substrates are non-covalently absorbed.
Assuntos
Carbono/química , Celulose/química , Cromatografia em Papel/métodos , Absorção , Cinamatos/isolamento & purificação , Especificidade por SubstratoRESUMO
A highly enantioselective (>95% ee) strategy to affect the desymmetrization of a maleimide has been performed by temporary attachment to an anthracene template followed by asymmetric reduction with an oxazaborolidine catalyst. A stereoablative over-reduction process was partially responsible for the high levels of enantioselectivity. Exemplification of the strategy by stereoselective functionalization and retro-Diels-Alder reaction provided the natural product pyrrolam A.