58928-95-3Relevant academic research and scientific papers
Highly enantioselective proton-initiated polycyclization of polyenes
Surendra, Karavadhi,Corey
supporting information; experimental part, p. 11992 - 11994 (2012/09/08)
This report describes the synthesis of a range of chiral polycyclic molecules (tricyclic to pentacyclic) from achiral polyene precursors by enantioselective proton-initiated polycyclization promoted by the 1:1 complex of o,o′-dichloro-BINOL and SbCl5. Excellent yields (ca. 90% per ring formed) and enantioselectivety (20:1 to 50:1) were obtained. The process is practical as well as efficient, because the chiral ligand is both readily prepared from R,R- or S,S-BINOL and easily recovered from the reaction mixture by extraction.
