A highly efficient alkenylation reaction of arylglyoxals with 3-vinylindoles catalyzed by chiral calcium phosphate is described. Structurally diverse allylic alcohols bearing indole and carbonyl units are prepared in excellent yields, good diastereoselectivities, and high to excellent enantioselectivities. These products are good building blocks for the synthesis of polysubstituted chiral tetrahydrocarbozol-2-ones. The mechanism study indicates that the most likely role of the catalyst is to activate the hydrate of arylglyoxal and control the stereoselectivity via desymmetric coordination.

An efficient asymmetric cyclization reaction of amino-acid-derived isothiocyanates with azodicarboxylates is described. The chiral 1,2,4-triazolines are prepared in good yield (up to 87%) and enantioselectivities (up to 95% ee).

The 3-vinyl indole is used as a nucleophile to react with aromatic and aliphatic imines. Chiral 3-substituted indoles bearing multiple functional groups are produced with up to 99% yield, a 98:2 E/Z ratio, and 97% ee. A possible mechanism is proposed to explain the observed stereoselectivities. This strategy provides an efficient way for the preparation of novel chiral 3-substituted indoles.

A simple Brønsted acid catalyzed tandem reaction, including intermolecular nucleophilic addition, substitution and intramolecular cyclization, in a one-pot manner is described. Thirty two 2-indolyl substituted carbazoles are generated in good to excellent yields. Based on this tandem reaction strategy, the poly(1,4-carbazole) is prepared for the first time. Preliminary studies indicate that the poly(1,4-carbazole) has good thermostability and optical properties.

The highly efficient, regioselective, and enantioselective transfer hydrogenation of α-keto ketimines and reductive amination of diketones by Brønsted acid catalysis is described. A series of chiral α-amino ketones is prepared in high yields (up to >99%), excellent regioselectivities (up to >99:1), and enantioselectivities (up to 98% ee). This method has broad substrate scope.

Two types of BINOL-related chiral aldehydes were used as organocatalysts for the direct α-functionalization of N-unprotected amino esters. The first chiral aldehyde catalysed α-alkylation of 2-aminomalonates with 3-indolylmethanols via imine activation was reported. Various tryptophan derivatives were produced in good yields and with high enantioselectivities. A reasonable mechanism was proposed and the core intermediates were identified by high resolution mass spectroscopy (HRMS).

This work describes an efficient α-alkylation reaction of α-amino aldehydes with 3-indolylmethanols. In the promotion of catalyst 3f, the target products were obtained in high yields (up to 99%), good diastereoselectivities (up to 88:12), and excellent enantioselectivities (up to 96% ee). The direct alkylation products can be readily converted into other tryptophan derivatives without the loss of stereoselectivities.

This paper describes a highly efficient [3 + 2] reaction between 3-vinylindoles and 3-indolylmethanols. Novel 2,3-bisindolylmethanes were prepared as single diastereoisomers in high yields with the promotion of 1 mol% 2-hydroxy-3,5-dinitrobenzoic acid.

An efficient aldol reaction of indole-3-carbaldehydes with ketones is described. O-TBS-protected l-threonine promoted the aldol addition of ketones to indole-3-carbaldehydes affording 3-indolylmethanols with good to excellent yields and diastereoselectivities, and excellent enantioselectivities.

An efficient DMAP catalyzed tandem aldol/imidization reaction of α-isothiocyanato esters with α-ketoamides is described, affording ring-fused thiocarbamates bearing contiguous quaternary carbon centers with up to 99% yield in a completely diastereoselective fashion. This method has a wide range of substrate scope and can be used in the synthesis of pyrrolidines.

The diastereoselectively switchable enantioselective Mannich reaction of isatin imines with hydroxyacetone is reported. The chiral primary amino acid catalyzed this Mannich reaction to afford both anti- and syn-Mannich adducts in high yields, good diastereoselectivities, and enantioselectivities. The reason for the solvent control of the diastereoselectivity phenomenon was investigated.

The H8−BINOL-derived, phosphoric acid catalyzed, highly enatioselective alkylation reaction of enamides with indolyl alcohols has been described. A phosphoric acid derived from H8-BINOL enabled an asymmetric α-alkylation of enamides with indolyl alcohols to give β-aryl 3-(3-indolyl)propanones in high yields (up to 96%) and with excellent enantioselectivity (up to 96% ee).

Two types of BINOL-related chiral aldehydes were used as organocatalysts for the direct α-functionalization of N-unprotected amino esters. The first chiral aldehyde catalysed α-alkylation of 2-aminomalonates with 3-indolylmethanols via imine activation was reported. Various tryptophan derivatives were produced in good yields and with high enantioselectivities. A reasonable mechanism was proposed and the core intermediates were identified by high resolution mass spectroscopy (HRMS).