Literature DB >> 16869668

Allylic disulfide rearrangement and desulfurization: mild, electrophile-free thioether formation from thiols.

David Crich1, Franck Brebion, Venkataramanan Krishnamurthy.   

Abstract

[reaction: see text] Secondary and tertiary allylic 2-pyridyl and 2-benzothiazolyl disulfides react with thiol groups at room temperature to give secondary and tertiary allyl alkyl disulfides. On the addition of a phosphine, a desulfurative sigmatropic rearrangement takes place at room temperature to give thioethers.

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Year:  2006        PMID： 16869668     DOI： 10.1021/ol061381+

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


  7 in total

1.  Chemoselective immobilization of peptides on abiotic and cell surfaces at controlled densities.

Authors:  Venkata R Krishnamurthy; John T Wilson; Wanxing Cui; XueZheng Song; Yi Lasanajak; Richard D Cummings; Elliot L Chaikof
Journal:  Langmuir       Date:  2010-06-01       Impact factor: 3.882

2.  Protecting group-free glycoligation by the desulfurative rearrangement of allylic disulfides as a means of assembly of oligosaccharide mimetics.

Authors:  Venkataraman Subramanian; Myriame Moumé-Pymbock; Tianshun Hu; David Crich
Journal:  J Org Chem       Date:  2011-03-23       Impact factor: 4.354

3.  One-pot thioether formation from S-nitrosothiols.

Authors:  Dehui Zhang; Nelmi O Devarie-Baez; Jia Pan; Hua Wang; Ming Xian
Journal:  Org Lett       Date:  2010-11-16       Impact factor: 6.005

4.  Sigmatropic rearrangements as tools for amino acid and peptide modification: application of the allylic sulfur ylide rearrangement to the preparation of neoglycoconjugates and other conjugates.

Authors:  David Crich; Yekui Zou; Franck Brebion
Journal:  J Org Chem       Date:  2006-11-24       Impact factor: 4.354

5.  Dechalcogenative allylic selenosulfide and disulfide rearrangements: complementary methods for the formation of allylic sulfides in the absence of electrophiles. Scope, limitations, and application to the functionalization of unprotected peptides in aqueous media.

Authors:  David Crich; Venkataramanan Krishnamurthy; Franck Brebion; Maheswaran Karatholuvhu; Venkataraman Subramanian; Thomas K Hutton
Journal:  J Am Chem Soc       Date:  2007-07-27       Impact factor: 15.419

6.  Silver-mediated allylic disulfide rearrangement for conjugation of thiols in protic media.

Authors:  David Crich; Venkataraman Subramanian; Maheswaran Karatholuvhu
Journal:  J Org Chem       Date:  2009-12-18       Impact factor: 4.354

7.  Labeling and Natural Post-Translational Modification of Peptides and Proteins via Chemoselective Pd-Catalyzed Prenylation of Cysteine.

Authors:  Thomas Schlatzer; Julia Kriegesmann; Hilmar Schröder; Melanie Trobe; Christian Lembacher-Fadum; Simone Santner; Alexander V Kravchuk; Christian F W Becker; Rolf Breinbauer
Journal:  J Am Chem Soc       Date:  2019-09-09       Impact factor: 15.419
  7 in total

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