A convenient strategy for the catalytic enantioselective dehydrative lactonization of allylic alcohols using a novel pi-acidic atropisomeric palladium-P,N-ligand complex of (S)-StackPhos for the synthesis of vinyl lactones is described. These optically pure vinyl lactones are abundant core skeleton found in a myriad of natural products that display an impressive range of biological activities. The method utilizes readily prepared allylic alcohols with liberation of water as the only byproduct, which also applies to the synthesis of broad range of substrates and extended to gamma-butenolides and gamma-butyrolactones. The reactions are high yielding, enantioselective, chemoselective, operationally simple, and produce heterocycles containing a synthetically useful vinyl group strategically positioned to enable transformations for target-oriented synthesis.

Enantioselective dehydrative lactonization of allylic alcohols via chiral pi-acid catalysis

ACS Spring Meeting 2021

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Enantioselective dehydrative lactonization of allylic alcohols via chiral </i><i>pi</i><i>-acid catalysis