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Experimental Diels–Alder Reactivities of Cycloalkenones and Cyclic Dienes Explained through Transition-State Distortion Energies^†

Corresponding Author

Dr. Robert S. Paton

[email protected]

Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA (UK)

Robert S. Paton, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA (UK)

K. N. Houk, Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095-1569 (USA)

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Dr. Seonah Kim,

Dr. Seonah Kim

Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095-1569 (USA)

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Audrey G. Ross,

Audrey G. Ross

Department of Chemistry, Columbia University, Havemeyer Hall, 3000 Broadway, New York, NY 10027 (USA)

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Prof. Samuel J. Danishefsky,

Prof. Samuel J. Danishefsky

Department of Chemistry, Columbia University, Havemeyer Hall, 3000 Broadway, New York, NY 10027 (USA)

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Prof. K. N. Houk,

Corresponding Author

Prof. K. N. Houk

[email protected]

Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095-1569 (USA)

Robert S. Paton, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA (UK)

K. N. Houk, Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095-1569 (USA)

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Dr. Robert S. Paton,

Corresponding Author

Dr. Robert S. Paton

[email protected]

Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA (UK)

Robert S. Paton, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA (UK)

K. N. Houk, Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095-1569 (USA)

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Dr. Seonah Kim,

Dr. Seonah Kim

Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095-1569 (USA)

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Audrey G. Ross,

Audrey G. Ross

Department of Chemistry, Columbia University, Havemeyer Hall, 3000 Broadway, New York, NY 10027 (USA)

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Prof. Samuel J. Danishefsky,

Prof. Samuel J. Danishefsky

Department of Chemistry, Columbia University, Havemeyer Hall, 3000 Broadway, New York, NY 10027 (USA)

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Prof. K. N. Houk,

Corresponding Author

Prof. K. N. Houk

[email protected]

Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095-1569 (USA)

Robert S. Paton, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA (UK)

K. N. Houk, Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095-1569 (USA)

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First published: 09 September 2011

https://doi.org/10.1002/ange.201103998

Citations: 27

^†

We are grateful to the John Fell Oxford University Press Research Fund (R.S.P) and the National Science Foundation (CHE-0548209 and Graduate Fellowship to A.G.R.) for financial support of this research. Computer time was provided in part by the UCLA Institute for Digital Research and Education (IDRE), by the Shared Research Computing Services Pilot (ShaRCS) project for the University of California Systems, and by the National Center for Supercomputing Applications on Cobalt, TG-CHE050044N, and Abe, TG-CHE090070.

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Graphical Abstract

Quantenchemische Rechnungen werden zur Untersuchung experimentell gemessener Reaktivitäten von cyclischen Dienen und Cycloalkenonen in Diels-Alder-Reaktionen verwendet. Die Wechselwirkungsenergien (rot) sind nahezu konstant; Unterschiede ergeben sich durch verschiedene Verzerrungsenergien von Dienophilen (blau) und Dienen (grün; siehe Bild, E_a=Aktivierungsenergie; Angaben in kcal mol⁻¹).

Supporting Information

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Volume123, Issue44

October 24, 2011

Pages 10550-10552

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Experimental Diels–Alder Reactivities of Cycloalkenones and Cyclic Dienes Explained through Transition-State Distortion Energies^†

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Experimental Diels–Alder Reactivities of Cycloalkenones and Cyclic Dienes Explained through Transition-State Distortion Energies†

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Experimental Diels–Alder Reactivities of Cycloalkenones and Cyclic Dienes Explained through Transition-State Distortion Energies^†