Stereoselective ring expansion via bicyclooxonium ion. A novel approach to oxocanes.
[reaction: see text] The stereoselective 1,4-rearrangement-ring expansion of tetrahydrofurans via bicyclo[3.3.0]oxonium ions was developed to synthesize oxocanes. On the basis of this rearrangement, the stereoselective synthesis of 2,8-syn-2,8-dimethyloxocane was accomplished.
Sakamoto
Yasuharu
Y
RIKEN (The Institute of Physical and Chemical Research), Wako, Saitama 351-0198, Japan.
Tamegai
Kyoko
K
Nakata
Tadashi
T