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

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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

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