Literature DB >> 15373480

Direct proline-catalyzed asymmetric alpha-aminoxylation of aldehydes and ketones.

Yujiro Hayashi1, Junichiro Yamaguchi, Tatsunobu Sumiya, Kazuhiro Hibino, Mitsuru Shoji.   

Abstract

The direct proline-catalyzed asymmetric alpha-aminoxylation of aldehydes and ketones has been developed using nitrosobenzene as an oxygen source, affording alpha-anilinoxy-aldehydes and -ketones with excellent enantioselectivity. Reaction conditions have been optimized, and low temperature (-20 degrees C) was found to be a key for the successful alpha-aminoxylation of aldehydes, while slow addition of nitrosobenzene is essential for that of ketones. The scope of the reaction is presented.

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Year:  2004        PMID： 15373480     DOI： 10.1021/jo049338s

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  6 in total

1.  Bronsted acid catalysis of achiral enamine for regio- and enantioselective nitroso aldol synthesis.

Authors:  Norie Momiyama; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2005-02-02       Impact factor: 15.419

2.  (±)-Cyclo-hexane-1,2-diyl bis-(4-nitro-benzoate).

Authors:  Sok Teng Tong; David Barker; Ka Wai Choi; Peter D W Boyd; Margaret A Brimble
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-10-22

3.  A sequential o-nitrosoaldol and Grignard addition process: an enantio- and diastereoselective entry to chiral 1,2-diols.

Authors:  Peng Jiao; Masanori Kawasaki; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  Continuous proline catalysis via leaching of solid proline.

Authors:  Suzanne M Opalka; Ashley R Longstreet; D Tyler McQuade
Journal:  Beilstein J Org Chem       Date:  2011-12-14       Impact factor: 2.883

Review 5.  Organocatalyzed asymmetric alpha-oxidation, alpha-aminoxylation and alpha-amination of carbonyl compounds.

Authors:  Tirayut Vilaivan; Worawan Bhanthumnavin
Journal:  Molecules       Date:  2010-02-11       Impact factor: 4.411

6.  Discovery of Furanone-Based Radiopharmaceuticals for Diagnostic Targeting of COX-1 in Ovarian Cancer.

Authors:  Md Jashim Uddin; Andrew J Wilson; Brenda C Crews; Paola Malerba; Md Imam Uddin; Philip J Kingsley; Kebreab Ghebreselasie; Cristina K Daniel; Michael L Nickels; Mohammed N Tantawy; Elma Jashim; H Charles Manning; Dineo Khabele; Lawrence J Marnett
Journal:  ACS Omega       Date:  2019-05-24
  6 in total

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