A bisperfluorotoluyl-BINOL catalyzed conjugate addition of trifluoroborate salts to doubly vinylogous esters and aldol condensation synthesized chiral δ-substituted cyclohexenones with high yields and enantioselectivities (10 examples, up to 89% yield,… Click to show full abstract
A bisperfluorotoluyl-BINOL catalyzed conjugate addition of trifluoroborate salts to doubly vinylogous esters and aldol condensation synthesized chiral δ-substituted cyclohexenones with high yields and enantioselectivities (10 examples, up to 89% yield, 89-98% ee). Stepwise and single-pot sequences were developed, with the former also providing β-substituted masked ketoaldehydes containing a vinyl ether. The transformation was used in a four-step total synthesis of penienone (24% overall yield), ≤ half the steps as in previous syntheses.
               
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