Enantioselective synthesis of spirocyclic cyclopentenes: asymmetric [3+2] annulation of 2-arylideneindane-1,3-diones with MBH carbonates derivatives catalyzed by multifunctional thiourea–phosphines

Advances in Annulation Reactions Initiated by Phosphorus Ylides Generated in situ

“…[19] Furthermore, the same research group also extended this methodology to 2-arylideneindane-1,3-diones for enantioselective synthesis of spirocyclic cyclopentenes (Scheme 26). [20] Scheme 25. Asymmetric ylide [3 + 2] …”

Applications of Chiral Phosphine‐Based Organocatalysts in Catalytic Asymmetric Reactions

“…Subsequently, they applied similar chiral phosphines to achieve the highly enantioselective [3+2] annulation of MBH carbonates with maleimides 21. Shi and co‐workers also developed a series of multifunctional thiourea phosphines derived from natural amino acids and applied them in the asymmetric [3+2] annulation of MBH carbonates with trifluoroethylidenemalonates,22 maleimides,23 and 2‐arylideneindane‐1,3‐diones 24. Liu and co‐workers reported an efficient Me‐DuPhos‐catalyzed asymmetric [3+2] cycloaddition reaction of MBH carbonates of isatins with N ‐phenylmaleimide 25.…”

Asymmetric Construction of Highly Functionalized Spirobarbiturate‐Cyclopentenes through Chiral Phosphine‐Catalyzed [3+2] Annulation of Morita–Baylis–Hillman Carbonates with Barbiturate‐Derived Alkenes

“…Barbas achieved the asymmetric [3+2] annulation of methylenebenzofuranone with MBH carbonates to give spirocyclopentene benzofuranones . Shi described the asymmetric [3+2] annulation of MBH carbonates with 2‐arylideneindane‐1,3‐diones to provide spirocyclopenteneindenediones . Chen and Liu used MBH carbonates of isatin for the asymmetric [3+2] annulation with alkenes to furnish cyclopentene‐fused spirocyclic heterocycles .…”