Literature DB >> 17284042

Aldehyde-selective Wacker oxidation in a thiyl-mediated vinyl group transfer route to daunosamine.

Gregory K Friestad1, Tao Jiang, Alex K Mathies.   

Abstract

[reaction: see text] Asymmetric dihydroxylation, thiyl radical mediated transfer of a silicon-tethered vinyl group to a hydrazone and an unconventional aldehyde-selective Wacker oxidation are sequenced for an efficient synthesis of methyl N-trifluoroacetyl-L-daunosaminide in 32% overall yield from crotonaldehyde.

Entities:  

Year:  2007        PMID： 17284042     DOI： 10.1021/ol063010z

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


  4 in total

1.  Peroxide-Mediated Wacker Oxidations for Organic Synthesis.

Authors:  Brian W Michel; Matthew S Sigman
Journal:  Aldrichimica Acta       Date:  2011       Impact factor: 3.667

2.  Catalyst-controlled Wacker-type oxidation of protected allylic amines.

Authors:  Brian W Michel; Jessica R McCombs; Andrea Winkler; Matthew S Sigman
Journal:  Angew Chem Int Ed Engl       Date:  2010-09-24       Impact factor: 15.336

3.  Effects of alpha-Alkoxy Substitution and Conformational Constraints on 6-exo Radical Cyclizations of Hydrazones via Reversible Thiyl and Stannyl Additions.

Authors:  Gregory K Friestad; Alex K Mathies
Journal:  Tetrahedron       Date:  2007-09-17       Impact factor: 2.457

Review 4.  Control of asymmetry in the radical addition approach to chiral amine synthesis.

Authors:  Gregory K Friestad
Journal:  Top Curr Chem       Date:  2014
  4 in total

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