Synlett 2019; 30(17): 1954-1965
DOI: 10.1055/s-0039-1689924
cluster
© Georg Thieme Verlag Stuttgart · New York

Development of a Hydrazine-Catalyzed Carbonyl-Olefin Metathesis Reaction

a  Department of Chemistry, Columbia University, New York, New York 10027, USA
b  Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, USA   Email: Tristan.lambert@cornell.edu
› Author Affiliations
The hydrazine catalysis research was funded by the National Science Foundation (CHE-0953259).
Further Information

Publication History

Received: 31 January 2019

Accepted after revision: 10 May 2019

Publication Date:
05 June 2019 (eFirst)

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

 
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