N-Heterocyclic carbene-catalyzed [4 + 2] cyclization of α,β-unsaturated carboxylic acids bearing γ-H with isatins: an enantioselective synthesis of spirocyclic oxindole–dihydropyranones

Ling Zhu, Chenxia Yu, Tuanjie Li, Yuhong Wang, Yi‐Nan Lu, Wenjing Wang, Changsheng Yao

Organic & Biomolecular Chemistry · 2015 · 44 citations · 41 references

Concepts

Abstract

An NHC-catalyzed asymmetric [4 + 2] annulation of isatins and α,β-unsaturated carboxylic acids bearing γ-H gave spirocyclic oxindole-dihydropyranones successfully via an in situ activation strategy. This protocol featured easy availability of raw materials, good yields and excellent enantioselectivities (up to 99% ee).

References

41