Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 13, Pages 5198-5206Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo200941r
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An expeditious synthetic approach to chiral phenol 1, a. key building block m the preparation of a series of drug candidates, is reported. The strategy includes a cost effective and readily scalable route to cyclopentanone 3 from isobutyronitrile (10). The sterically hindered and enolizable ketone 3 was subsequently employed in a challenging Grignard addition mediated by LaCl(3)center dot 2LiCl. A novel preparation of the lanthanide reagent required for this transformation is described. To complete the process, a highly enantioselective hydrogenation step afforded the target (1). The importance of the phenol group to the success of this asymmetric transformation is discussed.
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