Abstract
A 3,3'-di(1-diphenylmethylpiperazinyl)methyl H8BINOL compound, (S)-11, was prepared from the Mannich-type reaction of (S)-H8BINOL with paraformaldehyde and 1-(diphenylmethyl)piperazine. This compound can catalyze the asymmetric reaction of alkyl and aryl alkynes with N-(diphenylphosphinoyl)imines in the presence of Et2Zn and Ti(OiPr)4. It exhibits unprecedented high enantioselectivity (up to 85% ee) for a simple alkyl alkyne addition to the N-(diphenylphosphinoyl)imines. The easy removal of the N-(dipehenylphosphinoyl) protecting groups makes this method practically useful for the asymmetric synthesis of chiral propargyl amines.
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