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| Type |
Poster Presentation |
| Area |
Organic Chemistry |
| Room No. |
Event Hall |
| Time |
4월 19일 (목요일) 11:00~12:30 |
| Code |
ORGN.P-567 |
| Subject |
Chiral Lewis Acid Catalyzed Asymmetric Synthesis of Cyclobutanone |
| Authors |
YUNA CHOI, Do Hyun Ryu*
Department of Chemistry, Sungkyunkwan University, Korea
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| Abstract |
Cyclobutane derivate is a structural core incorporated into a wide range of natural products. Therefore, considerable attention has been devoted to the development of asymmetric methodologies for the synthesis of cyclobutane products. Consequently, over the past several decades, [2+2] cycloadditions of various alkenes have been established to access chiral cyclobutanes. Especially, in recent years, cyclobutanone is one of the most versatile chemical candidate for the functionalized cyclobutanes through various chemical transformation. However, [2+2] cycloaddition for the preparation of cyclobutanone was rarely been reported. In addition, there are very limited examples to synthesize chiral cyclobutanones. In this reason, highly efficient synthetic methodology was required for optically enriched functionalized cyclobutanones. In here, we report enantioselective synthesis of cyclobutanone catalyzed by chiral oxazaborolidinium ion (COBI) catalyst with various α-aryl and α-alkyl diazoesters. A wild range of cyclobutanone possessing β-quaternary chiral carbon were obtained in high yield (up to 91%) and excellent enantioselectivity (up to 98%) and diastereoselectivity (up to >20 : 1). |
| E-mail |
dbsk7442@nate.com |
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121st General Meeting of the KCS