Highly enantioselective access to diketopiperazines via cinchona alkaloid catalyzed Michael additions.

Highly enantioselective access to diketopiperazines via cinchona alkaloid catalyzed Michael additions† †Electronic supplementary information (ESI) available: Experimental procedures, analytical data and NMR spectra, X-ray data. CCDC 977363, 977364, 977365 and 1017592. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4sc03218g

Highly enantioselective Michael addition of 3-arylthio- and 3-alkylthiooxindoles to nitroolefins catalyzed by a simple cinchona alkaloid derived phosphoramide.

A new cinchona alkaloid derived bifunctional tertiary amine-phosphoramide is identified as a highly enantioselective catalyst for Michael addition of both unprotected 3-arylthio- and 3-alkylthiooxindoles to nitroolefins. The phosphoramide moiety of plays an indispensable role in this reaction.

Asymmetric organocatalytic Michael addition of ketones to vinyl sulfone.

Highly enantioselective organocatalytic Michael addition of ketones to vinyl sulfone catalyzed by a cinchona alkaloid-derived primary amine is reported for the first time; the described synthetic methodology was applied to the synthesis of sodium cyclamate.

Catalytic asymmetric sulfenylation to structurally diverse dithioketals.

We report the first example of the highly enantioselective synthesis of structurally diverse chiral dithioketals via asymmetric sulfenylation of various types of S-based nucleophiles, catalyzed by a cheap cinchona alkaloid derivative, dihydroquinine.

Enantioselective organocatalytic Michael additions to acrylic acid derivatives: generation of all-carbon quaternary stereocentres.

Acrylic esters, thioesters and N-acryloyl pyrrole have been identified as effective electrophiles in the enantioselective Michael addition reaction with beta-keto ester pro-nucleophiles catalysed by a cinchona alkaloid derived bifunctional organocatalyst; enantiomeric excesses of up to 98% and yields of up to 96% can be obtained for a range of Michael acceptors and pro-nucleophiles.