New Camphor-Derived Selenonium Ylides: Enantioselective Synthesis of Chiral Epoxides

Xin-Liang Li; Yi Wang; Zhi-Zhen Huang

doi:10.1071/CH05157

RESEARCH ARTICLE

Previous Next Contents Vol 58(10)

New Camphor-Derived Selenonium Ylides: Enantioselective Synthesis of Chiral Epoxides

Xin-Liang Li ^A , Yi Wang ^A and Zhi-Zhen Huang ^A ^B

+ Author Affiliations

- Author Affiliations

^A School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China.

^B Corresponding author. Email: huangzhizhen0226@163.com

Australian Journal of Chemistry 58(10) 749-752 https://doi.org/10.1071/CH05157
Submitted: 1 July 2005 Accepted: 19 August 2005 Published: 8 November 2005

Abstract

Optically pure selenonium salts 3 as the precursors of two new chiral selenonium ylides 4 can be synthesized stereoselectively from natural d-camphor in good yields. It is found that the reaction of the selenonium salt 3b, an aldehyde, and potassium tert-butoxide can take place smoothly in ‘one-pot’ via the formation of selenonium ylide 4b, to give chiral trans-diaryl epoxides 5 in good yields with good diastereoselectivities and enantioselectivities.

Acknowledgments

We gratefully acknowledge the National Natural Science Foundation of China for its financial support of the project 20332050.

References

New Camphor-Derived Selenonium Ylides: Enantioselective Synthesis of Chiral Epoxides

Abstract

Acknowledgments

Subscriber Login