Palladium-Catalyzed Efficient Enantioselective Synthesis
of Chiral Allenes: Steric and Electronic Effects of Ligands
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Abstract
Asymmetric synthesis of chiral allenes
starting from prochiral
substrates under mild reaction conditions promoted by Pd-SYNPHOS catalyst
is reported. This protocol provides an efficient access to various
enantioenriched aryl- and alkyl- substituted allenes, which are versatile
building blocks of high utility to both organic and medicinal chemists,
in excellent isolated yields (up to 96%) and high enatiomeric ratio
values (up to 95:5). In addition, a comparative study using several <i>C</i><sub>2</sub>-symmetric atropisomeric diphosphine ligands
revealed the overwhelming impact of the steric and electronic properties
of the ligands for the catalytic efficiency of this process
