Cross-coupling for cross-conjugation: practical synthesis and Diels-Alder reactions of [3]dendralenes.
The parent [3]dendralene and 2-substituted [3]dendralenes are made easily through cross-coupling reactions. Contrary to some earlier reports, [3]dendralene is sufficiently stable to be handled using standard synthetic methods. These compounds allow the one-step stereoselective construction of polycyclic frameworks through reactions with dienophiles. Site selectivity and stereoselectivity in Diels-Alder reactions with dienophiles are generally not influenced by the nature of the [3]dendralene's 2-substituent; these features can, however, be influenced with Lewis acids.
Bradford
Tanya A
TA
Research School of Chemistry, The Australian National University, Canberra ACT 0200, Australia.
Payne
Alan D
AD
Willis
Anthony C
AC
Paddon-Row
Michael N
MN
Sherburn
Michael S
MS