Carbonyl Allylation and Crotylation: Historical Perspective, Relevance to Polyketide Synthesis, and Evolution of Enantioselective Ruthenium-Catalyzed Hydrogen Auto-Transfer Processes
Michael J. Krische, Eliezer Ortiz, Connor Saludares, Jessica Wu, Yoon Cho, Catherine G. Santana
Abstract
Abstract The evolution of methods for carbonyl allylation and crotylation of alcohol proelectrophiles culminating in the design of iodide-bound ruthenium-JOSIPHOS catalysts is prefaced by a brief historical perspective on asymmetric carbonyl allylation and its relevance to polyketide construction. Using gaseous allene or butadiene as precursors to allyl- or crotylruthenium nucleophiles, respectively, new capabilities for carbonyl allylation and crotylation have been unlocked, including stereo- and site-selective methods for the allylation and crotylation of 1,3-diols and related polyols. 1 Introduction and Historical Perspective 2 Ruthenium-Catalyzed Conversion of Lower Alcohols into Higher Alcohols 3 Conclusion and Future Outlook