Enantioselective Functionalization of Prochiral Cyclobutanones and Cyclobutenones

Abstract

Enantioselective synthesis of cyclobutane derivatives is still a challenging topic in asymmetric synthesis. [2+2] Cycloaddition and skeleton rearrangement are two primary strategies to this end. Recently, functionalization of cyclobutanones and cyclobutenones, which are readily available via [2+2] cycloadditions as prochiral substrates, has emerged as a powerful tool to access versatile four-membered ring compounds. Herein, we summarize some recent advances in these areas from our and other groups.

1 Introduction

2 Enantioselective Functionalization of Cyclobutanones

2.1 Chiral Lithium Amide Approach

2.2 Enamine Approach

3 Enantioselective Functionalization of Cyclobutenones

4 Conclusion

Key words

cyclobutanone - cyclobutenone - desymmetrization - conjugate addition - chiral lithium amide - enantioselective reduction

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