Perrhenate Esters as Intermediates in Molecular Complexity-Increasing Reactions

Abstract

Allylic alcohols form perrhenate esters upon reaction with Re₂O₇ or HOReO₃. These species undergo nonstereospecific and nonregiospecific alcohol-transposition reactions through cationic intermediates. Sequencing these nonselective processes with reversible trapping by electrophiles results in cyclization reactions where regio- and stereocontrol are dictated by thermodynamics. The cationic intermediates can also be utilized as electrophiles in intra- or intermolecular dehydrative reactions with nucleophiles. These processes serve as the basis for applications in catalytic syntheses of a wide range of heterocyclic and carbocyclic structures that often show considerable increases in molecular complexity. This Account describes a sequence of events that started from a need to solve a problem for the completion of a natural product synthesis and evolved into a central element in the design of numerous new transformations that proceed under mild conditions from readily accessible substrates.

1 Introduction

2 Exploratory Studies

3 Application to Spiroketal Synthesis

4 Reactions with Epoxides as Trapping Agents

5 Development of Dehydrative Cyclizations

6 Bimolecular Reactions

7 Spirocyclic Ether Formation

8 Conclusions

Key words

allylic alcohols - transposition - perrhenate esters - rhenium catalysis - stereoselectivity - molecular complexity

Publication History

Received: 18 December 2020

Accepted after revision: 28 January 2021

Accepted Manuscript online:
28 January 2021

Article published online:
18 February 2021

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