Literature DB >> 15669834

Vanadium-catalyzed asymmetric oxidation of alpha-hydroxy esters using molecular oxygen as stoichiometric oxidant.

Alexander T Radosevich1, Christine Musich, F Dean Toste.   

Abstract

A vanadium-catalyzed method for the oxidative kinetic resolution of alpha-hydroxyesters, using oxygen as the terminal oxidant, is described. The catalyst is generated in situ from vanadium(V) tri-iso-propoxyoxide in combination with a tridentate ligand derived from 3,5-di-tert-butylsalicylaldehyde and (S)-tert-leucinol. The reaction allows for the enantioselective synthesis of both aromatic and aliphatic secondary alcohols, including those containing olefins and alkynes.

Entities:  

Year:  2005        PMID： 15669834     DOI： 10.1021/ja0433424

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  11 in total

1.  Effect of Ancillary Ligand on Electronic Structure as Probed by 51V Solid-State NMR Spectroscopy for Vanadium-o-Dioxolene Complexes.

Authors:  Olga Goncharova-Zapata; Pabitra B Chatterjee; Guangjin Hou; Laurence L Quinn; Mingyue Li; Jenna Yehl; Debbie C Crans; Tatyana Polenova
Journal:  CrystEngComm       Date:  2013-11-21       Impact factor: 3.545

2.  Chiral N-salicylidene vanadyl carboxylate-catalyzed enantioselective aerobic oxidation of alpha-hydroxy esters and amides.

Authors:  Shiue-Shien Weng; Mei-Wen Shen; Jun-Qi Kao; Yogesh S Munot; Chien-Tien Chen
Journal:  Proc Natl Acad Sci U S A       Date:  2006-02-24       Impact factor: 11.205

3.  Non-oxidative vanadium-catalyzed C-O bond cleavage: application to degradation of lignin model compounds.

Authors:  Sunghee Son; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2010-05-17       Impact factor: 15.336

4.  A Highly Selective Vanadium Catalyst for Benzylic C-H Oxidation.

Authors:  Ji-Bao Xia; Kevin W Cormier; Chuo Chen
Journal:  Chem Sci       Date:  2012-04-13       Impact factor: 9.825

5.  Silyl glyoxylates. Conception and realization of flexible conjunctive reagents for multicomponent coupling.

Authors:  Gregory R Boyce; Stephen N Greszler; Jeffrey S Johnson; Xin Linghu; Justin T Malinowski; David A Nicewicz; Andrew D Satterfield; Daniel C Schmitt; Kimberly M Steward
Journal:  J Org Chem       Date:  2012-03-23       Impact factor: 4.354

6.  An Oxidative Dearomatization Approach to Tetrodotoxin via a Masked ortho-Benzoquinone.

Authors:  Jacob G Robins; Jeffrey S Johnson
Journal:  Org Lett       Date:  2021-12-30       Impact factor: 6.005

7.  The palladium-catalyzed aerobic kinetic resolution of secondary alcohols: reaction development, scope, and applications.

Authors:  David C Ebner; Jeffrey T Bagdanoff; Eric M Ferreira; Ryan M McFadden; Daniel D Caspi; Raissa M Trend; Brian M Stoltz
Journal:  Chemistry       Date:  2009-12-07       Impact factor: 5.236

8.  Self-consistent synthesis of the squalene synthase inhibitor zaragozic acid C via controlled oligomerization.

Authors:  David A Nicewicz; Andrew D Satterfield; Daniel C Schmitt; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2008-12-24       Impact factor: 15.419

9.  Enantioselective C-H Olefination of α-Hydroxy and α-Amino Phenylacetic Acids by Kinetic Resolution.

Authors:  Kai-Jiong Xiao; Ling Chu; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2016-01-22       Impact factor: 15.336

10.  Vanadium-catalyzed regioselective oxidative coupling of 2-hydroxycarbazoles.

Authors:  Lei Liu; Patrick J Carroll; Marisa C Kozlowski
Journal:  Org Lett       Date:  2015-01-15       Impact factor: 6.005
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