In efforts to functionalize N-Boc 2-allylpyrrolidine to an alpha,beta-unsaturated phenyl ketone, we studied its cross metathesis with phenyl vinyl ketone, 1-phenylallyl alcohol and 1-phenylallyl acetate using the second-generation Grubbs catalyst. The only successful cross metathesis reaction occurred between N-Boc 2-allylpyrrolidine and 1-phenylallyl acetate (75% yield). Undesirable reactions involved the self-dimerization of phenyl vinyl ketone, and the unexpected conversion of 1-phenylallyl alcohol to propiophenone.

Alkene cross metathesis reactions with <i>N</i>-Boc 2-allylpyrrolidine

243rd National Meeting (2012)

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Alkene cross metathesis reactions with N-Boc 2-allylpyrrolidine