Cyclopentanones and their derivatives are treated as valuable fine chemicals due to their wide presence in nature, and because many of them display important biological activities. A vast number of natural and synthetic cyclopentanone derivatives have found applications as pharmaceuticals, perfumes and agricultural chemicals. This cyclopentanone structural motif is found as its original ketone form or further derivatized form in different prostaglandins, steroids, terpenoids, antibiotics, jasmonates etc. Due to a wide range of applications, efforts have been directed towards the synthesis of various cyclopentanone derivatives. Though the first report on the synthesis of cyclopentanone was reported long ago in 1925, great interest in developing methodologies for the synthesis of various substituted cyclopentanone derivatives has been seen in the last two decades. A wide number of paths have been chosen to access the different substituted cyclopentanone derivatives.<br/>As a part of our ongoing research in exploring various methodologies involving ketene chemistry, herein we report the development of an efficient asymmetric synthetic methodology for accessing pharmaceutically important and diversely substituted cyclopentanones. The work illustrates a novel dual Lewis acidic cooperative catalytic system that provides access to enantioenriched cyclopentanones from donor-acceptor cyclopropanes and ketenes. An in-situ ketene generation variant has also been developed. Readily available starting materials, a simple and straightforward one-pot reaction approach, and scalable reaction conditions are some of the benefits of the currently developed methodology.

Access to diversely substituted cyclopentanones via catalytic cyclopropane-ketene cycloaddition

ACS Fall 2021

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