Literature DB >> 17335227

An efficient and general approach to beta-functionalized ketones.

Jingliang Jiao1, Larry X Nguyen, Dennis R Patterson, Robert A Flowers.   

Abstract

[structure: see text]. The oxidation of selected anions (N3-, SCN-, I-, and Br-) by ceric ammonium nitrate (CAN) in the presence of substituted cyclopropyl alcohols provides a novel approach to beta-functionalized ketones. The protocol has a number of advantages including short reaction times, ease of reagent handling, and mild, neutral reaction conditions. Overall, this method provides an alternative pathway to important starting materials and intermediates in organic synthesis.

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Year:  2007        PMID： 17335227      PMCID： PMC2593908          DOI： 10.1021/ol070159h

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


  12 in total

1.  N-aminoimidazole derivatives inhibiting retroviral replication via a yet unidentified mode of action.

Authors:  Irene M Lagoja; Christophe Pannecouque; Arthur Van Aerschot; Myriam Witvrouw; Zeger Debyser; Jan Balzarini; Piet Herdewijn; Erik De Clercq
Journal:  J Med Chem       Date:  2003-04-10       Impact factor: 7.446

2.  Copper-mediated cross-coupling of functionalized arylmagnesium reagents with functionalized alkyl and benzylic halides.

Authors:  W Dohle; D M Lindsay; P Knochel
Journal:  Org Lett       Date:  2001-09-06       Impact factor: 6.005

3.  Metal-catalyzed release of supported boronic acids for C-C bond formation.

Authors:  C Pourbaix; F Carreaux; B Carboni
Journal:  Org Lett       Date:  2001-03-22       Impact factor: 6.005

4.  Sequential one-pot InBr(3)-catalyzed 1,4- then 1,2-nucleophilic addition to enones.

Authors:  Marco Bandini; Pier Giorgio Cozzi; Massimo Giacomini; Paolo Melchiorre; Simona Selva; Achille Umani-Ronchi
Journal:  J Org Chem       Date:  2002-05-31       Impact factor: 4.354

5.  The first conversion of primary alkyl halides to nitroalkanes under aqueous medium.

Authors:  Roberto Ballini; Luciano Barboni; Guido Giarlo
Journal:  J Org Chem       Date:  2004-10-01       Impact factor: 4.354

6.  Synthesis and pharmacological properties of benzamide derivatives as selective serotonin 4 receptor agonists.

Authors:  Shuji Sonda; Kenichi Katayama; Toshio Kawahara; Noriko Sato; Kiyoshi Asano
Journal:  Bioorg Med Chem       Date:  2004-05-15       Impact factor: 3.641

7.  Solvent-dependent chemoselectivities in additions of beta-carbonyl imines to allyltrimethylsilane with CTAN.

Authors:  Yang Zhang; Andrew J Raines; Robert A Flowers
Journal:  J Org Chem       Date:  2004-09-17       Impact factor: 4.354

8.  A novel class of phosphonate nucleosides. 9-[(1-phosphonomethoxycyclopropyl)methyl]guanine as a potent and selective anti-HBV agent.

Authors:  Jong-Ryoo Choi; Dong-Gyu Cho; Kee Y Roh; Jae-Taeg Hwang; Sinbyoung Ahn; Hyun S Jang; Woo-Young Cho; Kyong W Kim; Young-Gyo Cho; Jeongmin Kim; Yong-Zu Kim
Journal:  J Med Chem       Date:  2004-05-20       Impact factor: 7.446

9.  Mechanistic investigation of substrate oxidation by Ce(IV) reagents in acetonitrile.

Authors:  Yang Zhang; Robert A Flowers
Journal:  J Org Chem       Date:  2003-05-30       Impact factor: 4.354

10.  Solvent-dependent chemoselectivities in Ce(IV)-mediated oxidative coupling reactions.

Authors:  Yang Zhang; Andrew J Raines; Robert A Flowers
Journal:  Org Lett       Date:  2003-06-26       Impact factor: 6.005
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  9 in total

1.  Synthesis of gamma-halogenated ketones via the Ce(IV)-mediated oxidative coupling of cyclobutanols and inorganic halides.

Authors:  Brian M Casey; Cynthia A Eakin; Robert A Flowers
Journal:  Tetrahedron Lett       Date:  2009-03-25       Impact factor: 2.415

2.  On the nature of the oxidative heterocoupling of lithium enolates.

Authors:  Brian M Casey; Robert A Flowers
Journal:  J Am Chem Soc       Date:  2011-07-08       Impact factor: 15.419

3.  Solvent-dependent oxidative coupling of 1-aryl-1,3-dicarbonyls and styrene.

Authors:  Brian M Casey; Cynthia A Eakin; Jingliang Jiao; Dhandapani V Sadasivam; Robert A Flowers
Journal:  Tetrahedron       Date:  2009-12-26       Impact factor: 2.457

4.  Regiocontrolled Wacker Oxidation of Cinnamyl Azides.

Authors:  Angela S Carlson; Cristian Calcanas; Ryan M Brunner; Joseph J Topczewski
Journal:  Org Lett       Date:  2018-03-02       Impact factor: 6.005

5.  Corrigendum to Solvent-dependent oxidative coupling of 1-aryl-1,3-dicarbonyls and styrene.

Authors:  Brian M Casey; Cynthia A Eakin; Jingliang Jiao; Dhandapani V Sadasivam; Robert A Flowers
Journal:  Tetrahedron       Date:  2010-07-24       Impact factor: 2.457

6.  Pharmacophore-Directed Retrosynthesis Applied to Rameswaralide: Synthesis and Bioactivity of Sinularia Natural Product Tricyclic Cores.

Authors:  Nathanyal J Truax; Safiat Ayinde; Khoi Van; Jun O Liu; Daniel Romo
Journal:  Org Lett       Date:  2019-09-09       Impact factor: 6.005

7.  Asymmetric β-arylation of cyclopropanols enabled by photoredox and nickel dual catalysis.

Authors:  Jianhua Wang; Xiaoxun Li
Journal:  Chem Sci       Date:  2022-02-17       Impact factor: 9.825

8.  Copper(II)-salt-promoted oxidative ring-opening reactions of bicyclic cyclopropanol derivatives via radical pathways.

Authors:  Eietsu Hasegawa; Minami Tateyama; Ryosuke Nagumo; Eiji Tayama; Hajime Iwamoto
Journal:  Beilstein J Org Chem       Date:  2013-07-11       Impact factor: 2.883

9.  Ag/Pyridine Co-Mediated Oxidative Arylthiocyanation of Activated Alkenes.

Authors:  De-Long Kong; Jian-Xun Du; Wei-Ming Chu; Chun-Ying Ma; Jia-Yi Tao; Wen-Hua Feng
Journal:  Molecules       Date:  2018-10-22       Impact factor: 4.411
  9 in total

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