Organocuprates have been used extensively in synthesis, particularly with alkynes as non-transferable ligands; however, alkynes are an important functional group in potent pharmaceutical drugs as well as their precursors. Therefore, an efficient enantioselective synthesis of alkyne-containing all-carbon stereogenic centers is needed. The bidentate Cu�NHC derived from the corresponding NHC�Ag complex efficiently and enantioselectively facilitates the addition of alkynylaluminum reagents to allylic phosphates   to obtain quaternary stereogenic centers as a single enantiomer. Alkynyl additions proceed with >98% site selectivity for the desired SN2' product; no competitive isobutyl addition product is observed.

Enantioselective synthesis of alkyne-substituted quaternary carbon stereogenic centers through NHC-Cu-catalyzed allylic substitution reactions with (i-Bu)<sub>2</sub>(alkynyl)aluminum reagents

243rd National Meeting (2012)

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Enantioselective synthesis of alkyne-substituted quaternary carbon stereogenic centers through NHC-Cu-catalyzed allylic substitution reactions with (i-Bu)2(alkynyl)aluminum reagents

Enantioselective synthesis of alkyne-substituted quaternary carbon stereogenic centers through NHC-Cu-catalyzed allylic substitution reactions with (i-Bu)₂(alkynyl)aluminum reagents