Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins

Abstract

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.

Keywords

• asymmetric catalysis
• cyclization reaction
• michael addition
• one-pot three-component reaction
• spirobarbiturates