Lewis and Brønsted Acid Catalyzed Allylboration of Carbonyl Compounds: From Discovery to Mechanism and Applications

Dennis G. Hall

doi:10.1055/s-2007-980384

ACCOUNT

Lewis and Brønsted Acid Catalyzed Allylboration of Carbonyl Compounds: From Discovery to Mechanism and Applications

Dennis G. Hall*
Department of Chemistry, University of Alberta, W5-07 Gunning-Lemieux Chemistry Centre, Edmonton, Alberta, T6G 2G2, Canada
Fax: +1(780)4928231; e-Mail: dennis.hall@ualberta.ca;

Abstract

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Abstract

The recent development of Lewis and Brønsted acid catalyzed manifolds for the allylboration of carbonyl compounds has opened doors towards an ideal carbonyl allylation methodology using stable and nontoxic allylic boronates as reagents. This Account relates our laboratory’s discovery of acid-catalyzed allylborations, mechanistic investigations of these new processes, and ongoing efforts by our group and others towards a general catalytic enantioselective allylboration methodology.

1 Introduction

2 Discovery and Development of Catalyzed Allylborations with 2-Alkoxycarbonyl Allylic Boronates

2.1 Lewis Acid Catalyzed Allylboration

2.2 Brønsted Acid Catalyzed Allylboration

3 Mechanistic Considerations

4 Stoichiometric Approaches to Enantiocontrolled Allylboration of Aldehydes

5 Catalytic Methods for Enantioselective Allylborations

6 Lewis Acid Catalyzed Additions of α-Substituted Allylic Boronates

7 Conclusion

Key words

allylations - boron - catalysis - Lewis acids - stereoselectivity

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References

References and Notes

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