American Chemical Society
ol102811x_si_006.cif (30.26 kB)

One-Pot Construction of Aza- or Oxa-Bridged Benzocycloheptanes from Readily Available 2,3-Allenyl Malonates or 2,3-Allenols and o-Iodobenzaldehyde or Imine

Download (30.26 kB)
posted on 2011-02-04, 00:00 authored by Qiankun Li, Xinpeng Jiang, Chunling Fu, Shengming Ma
A Pd(OAc)2-catalyzed reaction of 2,3-alkadienyl malonates or 2,3-allenols with o-iodobenzaldehyde or its N-tosyl imine occurred smoothly in MeCN at 80 °C to form the oxa- or aza-bridged benzocycloheptane derivatives with important biological potential. With the optically active 2,3-allenols, the absolute configurations of all the three chiral centers have been conveniently established.