Electrophilic Metal Homoenolates and Their Application in the Synthesis of Cyclopropylamines

Abstract

Since their discovery, metal homoenolates have been widely explored as carbon-based nucleophiles for the β-functionalization of carbonyl derivatives. Only recently has it been reported that metal ­homoenolates can react as carbonyl electrophiles. In this context, we have recently discovered that cyclopropylamines can be prepared from cyclopropanols via zinc homoenolate intermediates. This Synpacts ­article will present an overview of the reactivity of homoenolates and our strategy to employ these intermediates for the synthesis of cyclopropylamines. Key mechanistic observations and their influence on reaction optimization will also be discussed.

1 Introduction

2 Homoenolates as Nucleophiles—Selected Reactivity

3 Homoenolates as Electrophilic Reagents

4 Conclusion

Key words

homoenolate - cyclopropanol - cyclopropylamine - amphoteric - zinc

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