Facile Diastereoselective Synthesis of Highly Substituted Alkylene‐oxetanes from 3‐Alkyl Allenoates and Diaryl 1,2‐Diones/α‐Ketoamides Mediated by DBU.

A facile tertiary amine‐mediated [2+2] annulation reaction of 3‐alkyl allenoates, and diaryl 1,2‐diones leading to diastereoselective synthesis of highly substituted alkylene‐oxetane derivatives is reported. The reaction was further extended to α‐ketoamides. The obtained amide‐appended oxetanes were transformed to 5‐methylene‐1H‐pyrrol‐2(5H)‐one derivatives with potential biological activity. A diastereoselective [2+2] cycloaddition reaction of 3‐alkyl allenoates and diaryl 1,2‐diones/α‐ketoamides mediated by tertiary amines leads to highly substituted alkylene‐oxetane derivatives. [ABSTRACT FROM AUTHOR]

Copyright of European Journal of Organic Chemistry is the property of Wiley-Blackwell and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)