Given the importance of indane derivatives in both organic and medicinal chemistry, the development of an effective synthetic protocol for the preparation of multifunctionalized 1,2,3-trisubstituted indane derivatives is of considerable interest. In this paper, we developed a cascade regio- and enantioselective double Michael addition to construct challenging multifunctionalized chiral indane derivatives in the presence of a bifunctional acid–base organocatalyst. The resulting optically active indane derivatives with three alternating trans stereocenters were produced in moderate to good yields with excellent diastereoselectivities and excellent enantioselectivities. Remarkably, the resulting products were facilely converted into multifunctionalized optically active (1-indanylmethyl)amine and tetrahydroindeno[2,1-b]pyrrole derivatives.

Chiral molecules containing sulfonyl and 1,5-diol moieties are useful synthetic blocks for various asymmetric transformations. A protocol has been developed for the enantioselective synthesis of optically active bis(β-hydroxy) sulfones catalyzed by a chiral cationic ruthenium diamine catalyst. A series of bis(β-hydroxy) sulfones have been obtained in excellent yields (up to 99%) with excellent enantioselectivities (up to 99%) as well as good diastereoselectivities (up to 99:1).

The spirocyclic pyrazolones are an important class of molecular structures with significant biological and pharmaceutical activities. Herein, we demonstrate that the combination of a Cinchona-based chiral primary amine and an ortho-fluorobenzoic acid is an efficient catalyst system for the double Michael addition of arylidenepyrazolones with α,β-unsaturated ketones, providing chiral unsymmetrical 6,10-diaryl-substituted spiro[cyclohexanone-pyrazolone] derivatives in high yields (up to 98%) with good diastereoselectivities and excellent enantioselectivities (up to 88:12 dr, 99% ee).

Pyrazoles are an important class of molecular structures with significant biological and pharmaceutical activities. Herein, heterocyclic compounds containing both a pyrazole motif and a masked amino acid structure are synthesized through the asymmetric Michael/aromatization of azlactones to α,β-unsaturated pyrazolones by using isosteviol-derived amine thiourea as the organocatalyst. The products are obtained in good yields (up to 93 %) with good diastereoselectivities and good enantioselectivities (up to >10:1 dr, 97 % ee).

(R)-1,1′-Binaphthyl-2,2′-diol (R-BINOL) derived chiral phosphoric acids have been explored as organocatalysts for the asymmetric oxidation of a series of aryl alkyl sulfides and 1,3-dithianes derived from aldehydes with aqueous hydrogen peroxide (H₂O₂) as the terminal oxidant. The enantiomerically enriched sulfoxides are obtained in moderate to excellent yield (up to 99%) with excellent diastereoselectivity (up to >99:1 dr) and moderate to good enantioselectivity (up to 91:9 er). In particular, the present protocol stereoselectively provides an efficient access to enantiomerically enriched aryl alkyl sulfoxides and dithioacetal mono-sulfoxides, which strictly restrains the formation of the undesirable by-products: sulfones or disulfoxides. The tracking experiments also verify that this approach proceeds via a direct sulfoxidation process, instead of a kinetic resolution route by overoxidation of the resulting sulfoxides.

Heterocyclic spirooxindoles that bear a multisubstitutedheterocyclic motif and quaternary stereocenter at the 3-position are prevalent in a large number of spirooxindole alkaloids, which are pharmaceutically relevant compounds with remarkable biological activities. In this paper, we report an efficient method for the construction of enantiomerically enriched spiro[2H-pyran-3,4′-indoline] derivatives by a systematic Michael/reduction/cyclization sequence. The initial Michael addition of isatylidenemalononitriles with ketones was catalyzed by a cinchona-based chiral primary amine and L-camphorsulfonic acid and furnished multifunctional, optically active Michael adducts in high yields (81–99 %) with excellent enantioselectivities (95 to >99 % ee). Subsequently, the Michael adducts were converted into spiro[2H-pyran-3,4′-indoline] derivatives in 52–93 % yields with 1.5:1 to 20:1 diastereomeric ratio and 90–99 % ee by utilizing NaBH₄ as a cascade reduction/cyclization reagent.

The asymmetric catalytic synthesis of naturally occurring and biologically active spiro compounds is a challenge for modern chemical methodology. Here we report the construction of spiro compounds through cascade [5+1] double Michael reactions between divinyl ketones and N-unprotectedoxindoles or N-phenyl-protected pyrazolones catalyzed by a combination of the easily available 9-amino-9-deoxy-epi-quinine with N-Boc-D-phenylglycine. The desired multistereogenic spiro[cyclohexanone-oxindoles and -pyrazolones] were obtained with high yields (up to 98 %) andstereoselectivities (up to >20:1 dr, 99 % ee).

Optically active hydrobenzoins are very important building blocks for further derivation of biologically active complexes, natural products, and pharmaceutical compounds. In this paper, A practical approach has been developed for asymmetric hydrogenation of benzils with Ru(OTf)(TsDPEN)(η⁶-cymene) as a pre-catalyst in methanol. Therefore, a series of chiral hydrobenzoins was synthesized in good yields with good to moderate diastereoselectivities and good to excellent enantioselectivities.

The enantioselective nitroaldol reactions of isatins with nitroalkanes were smoothly carried out by organocatalysis. A C6′-OH cinchona alkaloid derivative bearing a C9-OBn group exhibited outstanding catalytic efficiency as an acid–base bifunctional catalyst for the nitroaldol reaction of isatins with nitromethane, providing 3-hydroxy-3-(nitromethyl)indolin-2-ones in good yields (90–98 %) and with good to high enantiomeric excess values (72–95 %). The resultant oxindole derivatives are highly important for the synthesis of related natural products and pharmaceutically active compounds.