Absolute Configuration Determination and Convenient Asymmetric Synthesis of cis-3-(9-Anthryl)cyclohexanol with Proline as a Catalyst |
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Authors: | Wysocki Jędrzej Kwit Marcin Gawronski Jacek |
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Institution: | Department of Chemistry, Adam Mickiewicz University, Poznan, Poland. |
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Abstract: | cis‐(3R)‐(9‐anthryl) derivative of cyclohexanol was conveniently obtained in enantiomerically pure form from 2‐cyclohexenone using asymmetric Michael addition of anthrone catalyzed by l ‐proline in a key step. The absolute configuration of the addition product was unequivocally determined by means of electronic circular dichroism measurements combined with calculation of the circular dichroism spectrum by using a density functional theory method. Chirality 24:833–839, 2012. © 2012 Wiley Periodicals, Inc. |
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Keywords: | asymmetric catalysis proline conjugate addition circular dichroism DFT calculations |
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