An enantioselective cascade for simultaneous generation of five quaternary stereocenters from fully substituted enones.

A highly enantioselective cascade reaction for the generation of five quaternary stereocenters in one-pot operation is reported for the first time in the history of organic synthesis. Cinchona-alkaloid derived hydrogen-bonding catalyst furnished structurally complex cascade products from simple substrates in excellent yields and stereoselectivities.

Diastereoselective Synthesis of Rauhut-Currier-Type Adducts via an Unexpected α-Addition of α,β-Unsaturated γ-Butyrolactams to Coumarin Derivatives.

A novel, base-catalyzed and highly diastereoselective direct Michael addition-isomerization sequence is presented for the efficient synthesis of Rauhut-Currier-type adducts. An unexpected α-addition of γ-butyrolactam onto the 3-acyl coumarin derivatives was observed rather than the γ-addition, which is more common. The adducts could further undergo hydrolysis/decarboxylation to generate the products which are equivalent to those obtained by α-addition of γ-butyrolactam onto the corresponding chalcones.