Polysubstituted enynes have been lithiated on the propargylic position, and transmetalation to the corresponding zinc reagents promotes an easy cyclization reaction leading to polysubstituted cyclopentylmethylzinc derivatives. This cyclization is stereospecific, and a single diastereoisomer is formed, even when a tertiary and a quaternary center are linked in the process. The reaction is considered to take place via a metallo-ene-allene process.
Stereoselective synthesis of linear and angular triquinanes skeletons via the zinca-ene-allene reactions
作者:Christophe Meyer、Ilane Marek、Jean-F. Normant
DOI:10.1016/0040-4039(95)02325-9
日期:1996.2
The zinca-ene-allene reaction allows a new diastereoselective and straightforward alternative to the angular and linear triquinane framework synthesis.