Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins have been developed to afford chiral dispiro[indene-pyrrolidine-pyrimidine]s. Through this strategy, the target products could be obtained in good to excellent yields with excellent stereoselectivities. In addition, the synthetic utility was verified through a gram-scale synthesis, one-pot three-component reactions and further transformation experiments of the products.

A squaramide-catalyzed asymmetric Michael/cyclization tandem reaction between 2-isothiocyanato-1-indanones and 2arylidene-1,3-indanediones was developed. Under this strategy, the corresponding chiral bispirocyclic indanone compounds containing two contiguous stereocenters were obtained under mild conditions in moderate to excellent yields (up to 99 %) and enantioselectivities (up to 98 % ee). In addition, further transformation experiments were achieved through the oxidation and methylation reactions of the product, which also confirmed the synthetic practicality of this synthetic strategy.