Phosphine-Catalyzed [2 + 4] Annulation of Allenoates with Thiazolone-Derived Alkenes: Synthesis of Functionalized 6,7-Dihydro-5<i>H</i>-pyrano[2,3-<i>d</i>]thiazoles

Chang Wang, Zhenzhen Gao, Leijie Zhou, Chunhao Yuan, Zhanhu Sun, Yumei Xiao, Hongchao Guo

Organic Letters · 2016 · 81 citations · 56 references

Concepts

Abstract

Phosphine-catalyzed [2 + 4] annulation of allenoates with thiazolone-derived alkenes has been achieved under mild conditions, giving biologically important 6,7-dihydro-5H-pyrano[2,3-d]thiazole derivatives in high to excellent yields. With the use of Kwon's phosphine as the chiral catalyst, optically active products were obtained in good yields with excellent enantioselectivities.

References

56