Modular synthesis of chiral homo- and heterotrisoxazolines. Improving the enantioselectivity in the asymmetric Michael addition of indole to benzylidene malonate

Authors

Meng Chun Ye, Shanghai Institute of Organic Chemistry Chinese Academy of Sciences
Bin Li, Shanghai Institute of Organic Chemistry Chinese Academy of Sciences
Jian Zhou, Shanghai Institute of Organic Chemistry Chinese Academy of Sciences
Xiu Li Sun, Shanghai Institute of Organic Chemistry Chinese Academy of Sciences
Yong Tang, Shanghai Institute of Organic Chemistry Chinese Academy of Sciences

Document Type

Article

Publication Date

7-22-2005

Abstract

A simple approach to a diverse set of chiral trisoxazolines is described. Deprotonation of bisoxazolines 2, followed by treatment of 2- chloromethyloxazolines 3, affords chiral trisoxazolines, including chiral homo- and hetero-trisoxazolines in good to high yields. These trisoxazolines are successfully applied in the asymmetric reaction of indole with benzylidene malonate, and ee's up to 93% were obtained. © 2005 American Chemical Society.

Publication Source (Journal or Book title)

Journal of Organic Chemistry

First Page

6108

Last Page

6110

Recommended Citation

Ye, M., Li, B., Zhou, J., Sun, X., & Tang, Y. (2005). Modular synthesis of chiral homo- and heterotrisoxazolines. Improving the enantioselectivity in the asymmetric Michael addition of indole to benzylidene malonate. Journal of Organic Chemistry, 70 (15), 6108-6110. https://doi.org/10.1021/jo050595m