Catalytic Asymmetric Synthesis of a Tertiary Benzylic Carbon Center via Phenol-Directed Alkene Hydrogenation

S Caille, R Crockett, K Ranganathan…

Index: Caille, Seb; Crockett, Rich; Ranganathan, Krishnakumar; Wang, Xiang; Woo, Jacqueline C. S.; Walker, Shawn D. Journal of Organic Chemistry, 2011 , vol. 76, # 13 p. 5198 - 5206

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Citation Number: 9

Abstract

An expeditious synthetic approach to chiral phenol 1, a key building block in 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 LaCl3· 2LiCl. A novel preparation of the lanthanide reagent required for this ...