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

被引：13

作者：

Craig, Robert A., II ^{[1
]}

Stoltz, Brian M. ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 32期

基金：

美国国家卫生研究院;

关键词：

Allylic alkylation; Diastereoselective; Enantioselective; Palladium-catalyzed; Phosphinooxazoline; ENANTIOSELECTIVE TOTAL-SYNTHESIS; OXAZOLINE-CONTAINING LIGANDS; QUATERNARY STEREOCENTERS; N-HETEROCYCLES; CONSTRUCTION; TERTIARY; CIS-2-AMINO-3,3-DIMETHYL-1-INDANOL; PHOSPHINOOXAZOLINES; HYDROSILYLATION; HYDROGENATION;

D O I：

10.1016/j.tetlet.2015.06.039

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

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.

引用

收藏

页码：4670 / 4673

页数：4

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