Catalytic Asymmetric Intermolecular Stetter Reactions of Enolizable Aldehydes with Nitrostyrenes: Computational Study Provides Insight into the Success of the Catalyst†
Daniel A. DiRocco
Department of Chemistry, Colorado State University, Fort Collins, CO 80526 (USA)
Search for more papers by this authorElizabeth L. Noey
Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095 (USA)
Search for more papers by this authorCorresponding Author
Prof. K. N. Houk
Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095 (USA)
K. N. Houk, Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095 (USA)
Tomislav Rovis, Department of Chemistry, Colorado State University, Fort Collins, CO 80526 (USA)
Search for more papers by this authorCorresponding Author
Prof. Tomislav Rovis
Department of Chemistry, Colorado State University, Fort Collins, CO 80526 (USA)
K. N. Houk, Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095 (USA)
Tomislav Rovis, Department of Chemistry, Colorado State University, Fort Collins, CO 80526 (USA)
Search for more papers by this authorDaniel A. DiRocco
Department of Chemistry, Colorado State University, Fort Collins, CO 80526 (USA)
Search for more papers by this authorElizabeth L. Noey
Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095 (USA)
Search for more papers by this authorCorresponding Author
Prof. K. N. Houk
Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095 (USA)
K. N. Houk, Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095 (USA)
Tomislav Rovis, Department of Chemistry, Colorado State University, Fort Collins, CO 80526 (USA)
Search for more papers by this authorCorresponding Author
Prof. Tomislav Rovis
Department of Chemistry, Colorado State University, Fort Collins, CO 80526 (USA)
K. N. Houk, Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095 (USA)
Tomislav Rovis, Department of Chemistry, Colorado State University, Fort Collins, CO 80526 (USA)
Search for more papers by this authorWe thank NIGMS for generous support of this research (GM 36700 to K.N.H. and GM 72586 to T.R.). T.R. thanks Amgen and Roche for unrestricted support. E.L.N. is grateful to the National Institutes of Health Chemistry-Biology Interface Training Program Grant (T32M008496). K.N.H. is grateful to the National Science Foundation (CHE-0548209) for financial support, to the UCLA Academic Technology Services (ATS) Hoffman2 and IDRE clusters for computational resources, and for the TeraGrid resources provided by NCSA (CHE-0400414).
Graphical Abstract
Fluor hilft: Ein fluoriertes Triazoliumsalz wurde entwickelt, das als Präkatalysator für die asymmetrische intermolekulare Stetter-Reaktion von enolisierbaren Aldehyden und Nitrostyrolen dient (siehe Schema). Die trans-Fluorierung der Katalysatorarchitektur führt zu einer unerreichten Reaktivität und Enantioselektivität in der gewünschten Reaktion. Eine DFT-Studie liefert Belege für eine elektrostatische Wechselwirkung als die Quelle der gesteigerten Enantioinduktion.
Supporting Information
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