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Synfacts 2007(10): 1054-1054  
DOI: 10.1055/s-2007-969007
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Synthesis of cis-α-Substituted Cycloalkanols via Dynamic Kinetic Resolution

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
R. FernÁndez*, A. Ros, A. Magriz, H. Dietrich, J. M. Lassaletta*
Universidad de Sevilla and Instituto de Investigaciones Quimicas (CSIC-Use), Sevilla, Spain; Bayer CropScience GmbH, Frankfurt am main, Germany
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Publikationsdatum:
07. November 2007 (online)

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Significance

Expanding upon their previous work on enantioselective transfer hydrogenation of α-substituted cyclic ketimines via dynamic kinetic resolution (DKR) (Adv. Synth. Catal. 2005, 347, 591) the authors report the highly diastereo- and enantioselective reduction of α-substituted ketones to afford cis-cycloalkanols. These products can then be transformed to the corresponding trans-cycloalkyl amines through Mitsunobu reaction followed by reduction of the azide with PPh3 or LiAlH4.