Development of a Hydrazine-Catalyzed Carbonyl-Olefin Metathesis Reaction

This manuscript is dedicated to Professor Tom Katz, Columbia University, for his contributions to olefin metathesis.

Published as part of the Cluster Metathesis beyond Olefins

Abstract

Carbonyl-olefin metathesis is a potentially powerful yet underexplored reaction in organic synthesis. In recent years, however, this situation has begun to change, most notably with the introduction of several different catalytic technologies. The development of one of those new strategies, based on hydrazine catalysts and a novel [3+2] paradigm for double bond metathesis, is discussed herein. First, the stage is set with a description of some potential applications of carbonyl-olefin metathesis and a discussion of alternative strategies for this intriguing reaction.

1 Introduction

2 Potential Applications of Carbonyl-Olefin Metathesis

3 Carbonyl-Olefin Metathesis Strategies

4 Direct (Type I): Non-Catalytic

5 Direct (Type I): Acid-Catalyzed

6 Indirect (Type II): Metal Alkylidenes

7 Indirect (Type III): Hydrazine-Catalyzed

8 Conclusion

Key words

carbonyl-olefin metathesis - hydrazines - 1,3-dipolar cycloadditions - azomethine imines - cycloreversion

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