252869-48-0Relevant articles and documents
Hexamethyldisilazanes mediated one-pot intramolecular Michael addition-olefination reactions leading to exo-olefinated bicyclo[6.4.0]dodecanes
Fujishima, Hiroshi,Takeshita, Hiroshi,Suzuki, Shuichi,Toyota, Masahiro,Ihara, Masataka
, p. 2609 - 2616 (2007/10/03)
A novel one-pot reaction for the synthesis of exo-olefinated bicyclo[6.4.0]dodecanes 23 has been developed on the basis of an intramolecular Michael reaction of phenylsulfonyl compounds 4 with potassium hexamethyldisilazide (KHMDS) and a sequential reaction with an excess of methoxymethyl chloride (MOMCl). By this reaction, an exo-olefin group was regioselectively introduced at the α-position to the carbonyl group in the 6-membered ring in high yield. The regioselective introduction of the olefin moiety could be envisaged to proceed through a Mannich-type reaction involving the aminomethylating agent 24, which, in turn, is generated in situ by the action of HMDS on MOMCl. The Royal Society of Chemistry 1999.