ERROR 1
ERROR 1
ERROR 2
ERROR 2
ERROR 2
ERROR 2
ERROR 2
Password and Confirm password must match.
If you have an ACS member number, please enter it here so we can link this account to your membership. (optional)
ERROR 2
ACS values your privacy. By submitting your information, you are gaining access to C&EN and subscribing to our weekly newsletter. We use the information you provide to make your reading experience better, and we will never sell your data to third party members.
The four-membered ring compound cyclobutenone has been used for the first time as the electron-poor dienophile component of a Diels-Alder reaction (J. Am. Chem. Soc., DOI: 10.1021/ja1056888). This development paves the way for making bicyclic cyclopentanones, lactones, and lactams, which abound in natural products and drugs but have been tough to access through Diels-Alder chemistry. Xiaohua Li and Samuel J. Danishefsky of Columbia University and Sloan-Kettering Institute for Cancer Research surmised that cyclobutenone’s ring strain might make it a more reactive dienophile than cyclopentenone or cyclohexenone, which both need activating groups to participate in the Diels-Alder reaction. Although Diels-Alder reactions of substituted cyclobutenones have been reported, no one had reported the reaction with cyclobutenone itself. By developing a mild route to cyclobutenone and finding a way to store it stably, Li and Danishefsky were able to explore its reactivity. As they suspected, it’s a highly reactive dienophile. In addition, ring expansions of their Diels-Alder products led to diverse bicyclic derivatives. “This is a valuable new reagent and transformation that I am sure others will now certainly begin to use,” says Boston College organic chemist Marc L. Snapper.
Join the conversation
Contact the reporter
Submit a Letter to the Editor for publication
Engage with us on Twitter