Enantioselective Construction of Spirooxindole Derivatives through [3+2] Annulation Catalyzed by a Bisthiourea as a Multiple‐Hydrogen‐Bond Donor

Yan Shi, Aijun Lin, Haibin Mao, Zhijie Mao, Weipeng Li, Hongwen Hu, Chengjian Zhu, Yixiang Cheng

Chemistry - A European Journal · 2012 · 45 citations · 37 references

Concepts

Abstract

Anything between ureas? Spiro[isoxazolidine-3,3'-oxindole]s have been constructed by employing methyleneindolinones and nitrones as the starting materials through [3+2] annulation catalyzed by a bisthiourea. Products with three contiguous stereocenters, including one spiroquaternary stereocenter, are obtained in good yields with excellent enantio- and diastereoselectivity. The bisthiourea catalyst acts as a multiple-hydrogen-bond donor to simultaneously activate both substrates.

References

37