Literature DB >> 20218638

Highly diastereoselective alpha-hydroxylation of Fox chiral auxiliary-based amide enolates with molecular oxygen.

Hodney Lubin1, Arnaud Tessier, Grégory Chaume, Julien Pytkowicz, Thierry Brigaud.   

Abstract

Using a trifluoromethylated oxazolidine (Fox) chiral auxiliary, the hydroxylation reaction of enolates was very efficiently performed under smooth and friendly conditions with molecular oxygen as oxidizer. This reaction occurred with an extremely high diastereoselectivity. After cleavage, the chiral auxiliary is efficiently recovered and highly valuable enantiopure oxygenated carboxylic acids and alcohols are released.

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Year:  2010        PMID： 20218638     DOI： 10.1021/ol100211s

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  3 in total

1.  Base mediated deprotection strategies for trifluoroethyl (TFE) ethers, a new alcohol protecting group.

Authors:  Qingliang Yang; Jon T Njardarson
Journal:  Tetrahedron Lett       Date:  2013-12-18       Impact factor: 2.415

2.  Evolution of an oxidative dearomatization enabled total synthesis of vinigrol.

Authors:  Qingliang Yang; Cristian Draghici; Jon T Njardarson; Fang Li; Brandon R Smith; Pradipta Das
Journal:  Org Biomol Chem       Date:  2014-01-14       Impact factor: 3.876

3.  Copper-Catalyzed Vinylogous Aerobic Oxidation of Unsaturated Compounds with Air.

Authors:  Hai-Jun Zhang; Alexander W Schuppe; Shi-Tao Pan; Jin-Xiang Chen; Bo-Ran Wang; Timothy R Newhouse; Liang Yin
Journal:  J Am Chem Soc       Date:  2018-04-09       Impact factor: 15.419
  3 in total

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