Prof. Do Hyun RYU of the Department of Chemistry succeeded in developing an asymmetric synthesis method of square carbon ring ketone compound using Lewis acid catalyst.
Chiral square carbon ring compounds have attracted much attention from academia and industry as core structure of natural products with various physiological activities. Until recently, some of the leading research groups in the world have published studies on the development of synthetic methods, but there is no report on the asymmetric synthesis of square carbon ring compounds through rearrangement of tri-ring aldehydes.
Using a non-metal Lewis acid catalyst, the team was able to synthesize quaternary carbon ring ketone compounds with high yield and stereoselectivity through cyclopronation/semipinacol rearrangement sequential reactions. The developed reaction is very efficient in terms of atom economy because it uses a simple starting material and produces only nitrogen gas byproducts.
"The synthesis of chiral square carbon ring ketone compounds through rearrangement of tri-ring aldehydes is a challenge that has not been solved for over 50 years," said Prof. RYU who led this research. “The significance of this study is that this is the first time to successfully use catalysts and suggests the results of experiments that can identify reaction mechanisms.”
Rectangular carbon ring ketone compounds are useful compounds that can be used for various ring expansion and ring opening reactions due to its ring strain and therefore, it is expected to be a very useful synthesis tool for short and easy synthesis.
The results of this study were selected as a cover paper for the Journal of the American Chemical Society (JACS; IF = 14.357).
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