Advances in 2-(Alkoxycarbonyl)allylboration
of Carbonyl Compounds and Other Direct Methods for the Preparation
of α-Exo-Alkylidene γ-Lactones

Tim G. Elford; Dennis G. Hall

doi:10.1055/s-0029-1218664

REVIEW

Advances in 2-(Alkoxycarbonyl)allylboration of Carbonyl Compounds and Other Direct Methods for the Preparation of α-Exo-Alkylidene γ-Lactones

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

Abstract

All articles of this category

Abstract

Reagents and methodologies allowing for direct preparation of α-exo-alkylidene γ-lactones are of great interest because of the multiple biological properties demonstrated by these natural and unnatural compounds. Relatively few simple and direct methods are available for the preparation of these important compounds, and these methods along with their applications in target-oriented and diversity-oriented synthesis are covered in this review focusing on the most recent advances in the literature.

1 Introduction

1.1 Importance of α-Exo-Methylene and α-Exo-Alkylidene γ-Lactones

1.2 Overview of Indirect Preparative Methods

2 Direct Preparative Methods by Additions of 2-(Alkoxycarbonyl)allylmetal Reagents to Aldehydes and Ketones

2.1 Thermal Additions of 2-(Alkoxycarbonyl)allyl Boronates

2.2 Lewis Acid Catalyzed Additions of 2-(Alkoxycarbonyl)allyl Boronates

2.3 Brønsted Acid Catalyzed Additions of 2-(Alkoxycarbonyl)allyl Boronates

2.4 Preparation of Libraries of α-Exo-Methylene γ-Lactones and Their Functionalization into α-Exo-Alkylidene γ-Lactones

3 Additions of Other 2-(Alkoxycarbonyl)allylmetal Reagents

4 Barbier-Type Additions with 2-(Alkoxycarbonyl)allyl Halides

5 Other Direct Methods

6 Conclusion

Key words

allylations - boron - catalysis - lactones - natural products

Full Text

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