The Work Of Pr Karl A. Scheidt Group Department of Chemistry, Northwestern UniVersity, Evanston.

Karl Scheidt was exposed to chemistry at a young age thanks to the influence of his father. He obtained his PhD with William Roush from Indiana University in After an NIH postdoctoral fellowship under the direction of David A. Evans (Harvard University), he joined the faculty of northwestern University (Evanston, IL, USA) in His research focuses on the development of new organic methodology and the synthesis of bioactive molecules. He is a recent Sloan Foundation Fellow and Novartis Lecturer as well as the recipient of awards from Abbott Laboratories, Amgen, AstraZeneca, Boehringer-Ingelheim, and 3M.

Synthesis of Tertiary â-Hydroxy Amides by Enolate Additions to Acylsilanes J. AM. CHEM. SOC. 2006, 128,

An unusual dianion equivalent from acylsilanes: Chem. Commun., 2008, 1926–1928

Highly Stereoselective Synthesis of Substituted g-Lactams from Acylsilanes Angew. Chem. Int. Ed. 2008, 47, 2294 –2297 J. AM. CHEM. SOC. 2009, 131, 8805–8814

Catalytic Enantioselective a-Acylvinyl Anion Reactions of Silyloxyallenes Angew. Chem. Int. Ed. 2007, 46, 7806 –7809 J. AM. CHEM. SOC. 2006, 128,

The use of N-diphenylphosphinyland N-tert-butanesulfinyl functional groups attenuates potentially competing aza-Brook rearrangements and therefore facilitates high yields of R-silylamines. Org. Lett.,2005,1403 Org. Lett.,2008,5227

General types of N- heterocyclic carbenes. Dieter Enders.Chem. Rev., 2007, 107, 5606–5655 Breslow intermediate

The Thiazolium-Catalyzed Sila-Stetter Reaction: Conjugate Addition of Acylsilanes to Unsaturated Esters and Ketones J. AM. CHEM. SOC. 2004, 126,

Conversion of r,â-Unsaturated Aldehydes into Saturated Esters Org. Lett.,2005,7,905

Tandem Oxidation of Allylic and Benzylic Alcohols to Esters Catalyzed by N-Heterocyclic Carbenes Org. Lett., 2007,9,371 Org. Lett.,2008,10,4331

Catalytic Conjugate Additions of Carbonyl Anions under Neutral Aqueous Conditions J. AM. CHEM. SOC.2005, 127,14675

A Highly Enantioselective Intramolecular Michael Reaction Catalyzed by N-Heterocyclic Carbenes ~99%ee

Angew. Chem. Int. Ed. 2007, 46, 3107 –3110

Direct Nucleophilic Acylation of Nitroalkenes Promoted by a Fluoride Anion/ Thiourea Combination J. AM. CHEM. SOC. 2006, 128, Our incorporation of a thiourea was based on the additions to nitroalkenes recently reported by Takemoto.

Hydroacylation of Activated Ketones Catalyzed by N-Heterocyclic Carbenes J. AM. CHEM. SOC. 2006, 128,

Nucleophilic Acylation of o-Quinone Methides: An Umpolung Strategy for the Synthesis of r-Aryl Ketones and Benzofurans

J. AM. CHEM. SOC. 2007, 129,

Enantioselective Synthesis of r,r-Disubstituted Cyclopentenes by an N-Heterocyclic Carbene-Catalyzed Desymmetrization of 1,3-Diketones Up to 96%ee

Proposed Reaction Pathway J. AM. CHEM. SOC. 2007, 129,

Highly Stereoselective Formal [3 + 3] Cycloaddition of Enals and Azomethine Imines Catalyzed by N-Heterocyclic Carbenes J. AM. CHEM. SOC. 2007, 129,

Direct Amination of Homoenolates Catalyzed by N-Heterocyclic Carbenes J. AM. CHEM. SOC. 2008, 130, Highly Diastereo- and Enantioselective Additions of Homoenolates to Nitrones Catalyzed by N-Heterocyclic Carbenes

J. AM. CHEM. SOC. 2008, 130, 2416

N-Heterocyclic Carbene-Catalyzed Enantioselective Mannich Reactions with r-Aryloxyacetaldehydes J. AM. CHEM. SOC. 2009, 131, 18028–18029

Catalytic Enantioselective Synthesis of Flavanones and Chromanones Up to 94% ee J. AM. CHEM. SOC. 2007, 129,

Cooperative N-Heterocyclic Carbene/Lewis Acid Catalysis for Highly Stereoselective Annulation Reactions with Homoenolates 98-99% ee

Proposed Catalytic Pathway We postulate that 2-propanol might accelerate the acylation step from III to regenerate the carbene catalyst and Ti(Oi-Pr)4 by facilitating the disassociation of the tertiary alkoxide. J. AM. CHEM. SOC. 2010, 132, 5345–5347 Breslow intermediate

Cooperative catalysis by carbenes and Lewis acids in a highly stereoselective route to g-lactams

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