•The first organocatalytic asymmetric synthesis of trispirooxindole was disclosed.•Trispirooxindoles were featured with trans-configuration.•Trispirooxindoles were featured with two quaternary stereocenters.An efficient stereoselective Michael-cyclization reaction of 3-isothiocyanato oxindoles to cyclic methyleneindolinones has been described. The protocol provides a facile and efficient access to chiral trans-configured trispirooxindoles containing two quaternary stereocenters in good yields (up to 89%) with good diastereoselectivities (up to 90:10) and high enantioselectivities (up to 94% ee) under mild conditions.

An efficient enantioselective Michael addition of benzofuran-2(3H)-ones to alkylideneindolenines generated in situ from arenesulfonylalkylindoles has been described, and a series of optically active C-3 alkyl-substituted benzofuran-2(3H)-one derivatives containing indole skeleton with two adjacent stereocenters have been obtained. The resulting adduct can readily be converted to chiral o-hydroxyphenylacetic acid derivative with indole motif.

A base-mediated Michael addition of carbon nucleophiles to vinylogous imine intermediates generated in situ from 3-(1-arylsulfonylalkyl)-7-azaindoles has been developed. A series of 3-sec-alkyl substituted 7-azaindoles have been obtained with high yields (up to 98%). Due to the relative inertness of the 3-position of 7-azaindole and the lack of some electrophiles in Friedel–Crafts reaction, this new protocol provides a more convenient and efficient approach to these valuable targets.

Michael addition of hetero-nucleophiles to active vinylogous imine intermediates generated in situ from 3-(1-arylsulfonylalkyl)-7-azaindoles has been described. This new strategy provides a facile and efficient approach to valuable 3-alkyl substituted 7-azaindole derivatives containing heteroatoms in high yields.

Enantioselective O-alkylation of α-nitrophosphonates was reported for the first time. A series of optically active 3,3-disubstituted oxindoles was prepared via a less exploited organocatalyzed stereoablative reaction of 3-bromooxindoles.

Enantioselective Michael addition of simple 3(2H)-furanones to α,β-unsaturated aldehydes has been described. The protocol provides a simple and efficient access to complex 3(2H)-furanones containing adjacent quaternary and tertiary stereocenters in high yields with moderate diastereoselectivities and excellent enantioselectivities.

An efficient stereoselective Michael addition of simple 3(2H)-furanones to α,β-unsaturated ketones has been described. The protocol provides a facile and efficient access to complex 3(2H)-furanones containing adjacent quaternary and tertiary stereocenters in high yields (up to 99%) with good diastereoselectivities (up to 86:14) and excellent enantioselectivities (up to 98% ee) under mild conditions.