Synthesis of Medium-Sized Cycloalkenes via Fused-Cyclobutenes

This book explains the existence of the intermediate using two approaches: computational chemistry and coordination chemistry. In this book, the author has developed new methods for synthesizing medium-sized cycloalkenes by utilizing the 4-electrocyclic reaction of fused-cyclobutenes. The fundamental and most important strategy and feature of the work are as follows: first, cyclobutene is used as a readily available raw material with high-strain energy to generate more strained medium-sized cis,trans-cycloalkadiene molecules. Second, by judiciously selecting the reaction conditions, the short-lived intermediate (medium-sized cis,trans-cycloalkadiene) can be converted to medium-sized cis- or trans-cycloalkenes. For the former, the generation of the medium-sized cis,trans-cycloalkadiene intermediate is greatly affected by the substituent on the cyclobutene, and there are few examples of its generation confirmed at room temperature. Regarding the latter, the synthesis of trans-cycloalkenes is noteworthy in terms of establishing a new synthetic methodology and providing one of the few asymmetric synthesis methods, which has not been achieved before. Readers of this book can gain novel insights into strained molecules involved not only in small-sized cycloalkenes but also in medium-sized ones.

Nominated as an outstanding Ph.D. thesis by Kyoto University Provides detailed introduction of the properties of cyclobutene and medium-sized trans-cycloalkene Explains detailed principle and provides a brief review of 4-electrocyclic reaction

Autorentext
Dr. Tomohiro is a researcher at the Department of Chemical Process Research and Development in ONO PHARMACEUTICAL CO., LTD. The author started his academic career as an undergraduate school student at the Department of Hospital Pharmacy at the University of Toyama and engaged in the discovery of hyaluronidase inhibitors from traditional plants. The author moved to Kyoto University and got his Ph.D. under the supervision of Dr. Kiyosei Takasu with the thesis titled, 'Synthetic Utility of Fused-Cyclobutenes: Synthesis of Medium-Sized Cycloalkenes.' The author s current interest is focused on greenery, cost-effective, and safe production of active pharmaceutical ingredients on an industrial scale.

Inhalt

Introduction.- Synthesis of Functionalized Medium-Sized trans-Cycloalkenes by 4 Electrocyclic Ring Opening Alkylation Cascade.- Synthesis of -Aryl Medium Sized Cyclic Enones by 4 Electrocyclic Ring Opening Heck Matsuda Arylation Sequence.- Asymmetric Organocatalytic [2+2] Cycloaddition Affording Bicyclo[n.2.0]alkenes.- Conclusion.- Experiments.