Literature DB >> 18336036

Catalytic asymmetric synthesis of allylic thiol derivatives.

Larry E Overman1, Scott W Roberts, Helen F Sneddon.   

Abstract

The palladium(II) complex [(Rp,S)-COP-Cl]2 and its enantiomer catalyze the rearrangement of linear prochiral O-allyl carbamothioates under mild conditions to provide branched S-allyl carbamothioates in high yield and high enantiomeric purity.

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Year:  2008        PMID： 18336036      PMCID： PMC3064473          DOI： 10.1021/ol8002942

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


  7 in total

1.  Palladium-catalyzed enantioselective allylic alkylation of thiocarboxylate ions: asymmetric synthesis of allylic thioesters and memory effect/dynamic kinetic resolution of allylic esters.

Authors:  Bernhard J Lüssem; Hans-Joachim Gais
Journal:  J Org Chem       Date:  2004-06-11       Impact factor: 4.354

2.  Palladium(0)-catalyzed enantioselective O,S-rearrangement of racemic O-allylic thiocarbamates: a new entry to enantioenriched allylic sulfur compounds.

Authors:  Hans-Joachim Gais; Achim Böhme
Journal:  J Org Chem       Date:  2002-02-22       Impact factor: 4.354

3.  Kinetic and computational analysis of the palladium(II)-catalyzed asymmetric allylic trichloroacetimidate rearrangement: development of a model for enantioselectivity.

Authors:  Mary P Watson; Larry E Overman; Robert G Bergman
Journal:  J Am Chem Soc       Date:  2007-04-03       Impact factor: 15.419

4.  Practical asymmetric synthesis of a potent Cathepsin K inhibitor. Efficient palladium removal following Suzuki coupling.

Authors:  Cheng-Yi Chen; Philippe Dagneau; Edward J J Grabowski; Renata Oballa; Paul O'Shea; Peppi Prasit; Joël Robichaud; Rich Tillyer; Xin Wang
Journal:  J Org Chem       Date:  2003-04-04       Impact factor: 4.354

5.  Monomeric cobalt oxazoline palladacycles (COP). Useful catalysts for catalytic asymmetric rearrangement of allylic trichloroacetimidates.

Authors:  Stefan F Kirsch; Larry E Overman; Mary P Watson
Journal:  J Org Chem       Date:  2004-11-12       Impact factor: 4.354

6.  Catalytic asymmetric rearrangement of allylic N-aryl trifluoroacetimidates. A useful method for transforming prochiral allylic alcohols to chiral allylic amines.

Authors:  Larry E Overman; Carolyn E Owen; Mary M Pavan; Christopher J Richards
Journal:  Org Lett       Date:  2003-05-29       Impact factor: 6.005

7.  Catalytic asymmetric rearrangement of allylic trichloroacetimidates. A practical method for preparing allylic amines and congeners of high enantiomeric purity.

Authors:  Carolyn E Anderson; Larry E Overman
Journal:  J Am Chem Soc       Date:  2003-10-15       Impact factor: 15.419
  7 in total
  5 in total

1.  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

2.  Promoter free allylation of trichloroacetimidates with allyltributylstannanes under thermal conditions to access the common 1,1'-diarylbutyl pharmacophore.

Authors:  Nivedita S Mahajani; John D Chisholm
Journal:  Org Biomol Chem       Date:  2018-05-30       Impact factor: 3.876

3.  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

4.  Synthesis of neoglycoconjugates by the desulfurative rearrangement of allylic disulfides.

Authors:  David Crich; Fan Yang
Journal:  J Org Chem       Date:  2008-08-27       Impact factor: 4.354

5.  Enantioselective synthesis and application to the allylic imidate rearrangement of amine-coordinated palladacycle catalysts of cobalt sandwich complexes.

Authors:  Doyle J Cassar; Gennadiy Ilyashenko; Muhammad Ismail; James Woods; David L Hughes; Christopher J Richards
Journal:  Chemistry       Date:  2013-11-21       Impact factor: 5.236
  5 in total

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