Diastereoselective reduction of acyclic N-aryl-β-amino ketones

Highly diastereoselective construction of acyclic systems with two adjacent quaternary stereocenters by allylation of ketones.

Unsymmetrical ketones and allyltitanocenes generated by the desulfurizative titanation of γ,γ-disubstituted allyl phenyl sulfides react under highly diastereoselective construction of adjacent quaternary stereocenters (see scheme; R(L) = large group, R(S) = small group). The title reaction is stereospecific: the anti- and syn-homoallylic alcohols are obtained by the reaction of E- and Z-allylic...

Efficient synthesis of β’-amino-α,β-unsaturated ketones

A general and simple procedure to access chiral β'-amino-α,β-enones, in seven steps, from an α,β unsaturated ester has been described. The use of a Horner-Wadsworth-Emmons reaction as a key step for generating the β'-amino-α,β-enones, permits access to a range of substrates under mild conditions and in moderate to high yield.

Direct β-functionalization of cyclic ketones with aryl ketones via the merger of photoredox and organocatalysis.

The direct β-coupling of cyclic ketones with aryl ketones has been achieved via the synergistic combination of photoredox catalysis and organocatalysis. Diaryl oxymethyl or aryl-alkyl oxymethyl radicals, transiently generated via single-electron reduction of ketone precursors, readily merge with β-enaminyl radical species, generated by photon-induced enamine oxidation, to produce γ-hydroxyketon...

An Easy and Efficient Method to Produce γ-Amino Alcohols by Reduction of β-Enamino Ketones

The synthesis of γ-amino alcohols 1 is of great interest due to the pharmacology of these compounds and their derivatives. This functionality is found in several antibiotics and other biologically active natural products. Several synthetic methods have been described for the synthesis of γ-amino alcohols 1 from diols, hydroxazols, lactams and lactones, but the more important methods are those w...

Synthesis of N-aryl β-amino acid derivatives via asymmetric hydrogenation