Control of hetero-diels-alder stereoselectivity through solvent polarity and bronsted or lewis acid catalysis; Theory and experiment

摘要

The stereoselectivity of cycloadditions involving 3-methyleneoxindole and 2-azadienes can be controlled by solvent polarity and by Lewis or Bronsted acid catalysis. The improvements in selectivity are advantageous for the synthesis of spiroquinazoline alkaloids such as alantrypinone and lapatin B.