Stereocontrolled Synthesis and Functionalization of Cyclobutanes and Cyclobutanones

Abstract

In the last decade a certain number of new cyclobutane and cyclobutanone synthesis and functionalization protocols have been published. Organo- and biocatalyzed eco-friendly approaches to cyclobutane-containing molecules have been developed with interesting results. Also, successful new total synthesis of bioactive compounds and drugs have been recently reported where a four membered ring represented the key intermediate. Therefore, the rising interest in this field represents a great point of discussion for the scientific community, disclosing the synthetic potential of strained four membered ring carbocyclic compounds. Herein we report a critical survey on the literature concerning the enantiocontrolled synthesis and functionalization of cyclobutane derivatives, with particular attention to metal-free, low impact methodologies, published during the period 2000–2013.

Keywords

• cyclobutanone
• cyclobutane
• stereocontrol
• ring enlargement
• alkylation
• organocatalysis
• cycloaddition
• biocatalysis
• stereochemistry
• oxidation