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Synfacts 2005(1): 0132-0132  
DOI: 10.1055/s-2005-872189
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Synthesis of 2-Aryl-4-piperidones

Contributor(s): Mark Lautens, Josephine Yuen
R. B. C. Jagt, J. G. de Vries, B. L. Feringa*, A. J. Minnaard
University of Groningen, The Netherlands
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Publikationsdatum:
21. September 2005 (online)

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Significance

A highly enantioselective synthesis of 2-aryl-4-piperidones is reported using a rhodium/phospharamidite-catalyzed conjugate addition of arylboroxines to 2,3-dihydro-4-pyridones. The enantioselectivity remains very high for both electron-rich and electron-deficient arylboroxines, although the yields are diminished with electron-poor arylboroxines.