Synthesis and exploration of electronically modified (R)-5,5-dimethyl-(p-CF3)3-i-PrPHOX in palladium-catalyzed enantio- and diastereoselective allylic alkylation: a practical alternative to (R)-(p-CF3)3-t-BuPHOX

TETRAHEDRON LETTERS

卷:56

Article

Craig, Robert A., II¹  Stoltz, Brian M.¹ 

[1] CALTECH, Warren & Katharine Schlinger Lab Chem & Chem Engn, Div Chem & Chem Engn, Pasadena, CA 91125 USA

关键词: Allylic alkylation;    Diastereoselective;    Enantioselective;    Palladium-catalyzed;    Phosphinooxazoline;   

DOI  :  10.1016/j.tetlet.2015.06.039

来源: Elsevier

【 摘 要 】

The synthesis of the novel electronically modified phosphinooxazoline (PHOX) ligand, (R)-5,5-dimethyl-(p-CF3)(3)-i-PrPHOX, is described. The utility of this PHOX ligand is explored in both enantio- and diastereoselective palladium-catalyzed allylic alkylations. These investigations prove (R)-5,5-dimethyl-(p-CF3)(3)-i-PrPHOX to be an effective and cost-efficient alternative to electronically modified PHOX ligands derived from the prohibitively expensive (R)-t-leucine. (C) 2015 Elsevier Ltd. All rights reserved.

【 授权许可】

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