Efficient Synthesis of Deoxybenzoins from Chalcones

Abstract

β‐Ketoaldehydes derived from chalcone epoxides by Lewis acid–catalyzed rearrangement underwent smooth deformylation when refluxed in tetrahydrofuran (THF) in the presence of ethylenediamine, affording deoxybenzoins in excellent yields. The method is general and useful for the preparation of deoxybenzoins with a variety of substitution patterns.

Keywords:

• chalcones
• epoxides
• deoxybenzoins
• deformylation
• rearrangement

Acknowledgments

This work was supported by Kerala State Council of Science, Technology, and Environment and Council of Scientific and Industrial Research, New Delhi [Project No. 01(1954)/04/EMR‐II]. We thank Madurai Kamaraj University, Madurai, for providing spectral and analytical data. P. M. thanks the University Grants Commission for assistance under the Faculty Improvement Program.