Reactions of Diketones and N-Allenoyloxazolidinones Catalyzed by Metal-Bis(oxazoline) Complexes
Contributors: Evans, David A.; Jacobsen, Eric N.; Ritter, Tobias
Published: 2012
Language: eng
Description: This dissertation describes the investigation of the utility of metal-bis(oxazoline) complexes in catalytic asymmetric reactions. The development of Cu(II)-catalyzed regio- and enantioselective additions of silylketenthioacetals into diketones is discussed in the first chapter. Cu(OTf)2(t-BuBox) complexes were found to be an effective catalyst with a broad substrate scope, providing tertiary alcohols in high yields, regioselectivities, and enantioselectivities. A model that accounts for the absolute stereochemistry of the product based on A1,3-interaction was proposed. Relative reactivities among diketones were also investigated.
Notes: Keywords: allenes, asymmetric reactions, bis(oxazoline), catalysis, diketones.

Thesis Ph.D. Harvard University 2012