Diels-Alder reactions of 2-alkenylboranes and cis-1-alkenylboranes. Anomalous selectivity that allows a choice of regiochemistry

Article abstract of DOI:10.1016/S0040-4039(00)93382-3

2-Alkenyl- and cis-1-alkenylboranes are highly reactive Diels-Alder dienophiles which display unusual selectivity patterns. By taking advantage of a reversal of regiochemistry of reactions with alkenyldihalo- versus alkenyldialkylboranes, any desired regioisomeric product may be favored, usually with very high selectivity.