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Resolution of topologically chiral molecular objects

1998; Wiley; Volume: 10; Issue: 1-2 Linguagem: Inglês

10.1002/chir.20

1520-636X

Jean‐Claude Chambron, Christiane Dietrich‐Buchecker, Gwénaël Rapenne, Jean‐Pierre Sauvage,

Surface Chemistry and Catalysis

ChiralityVolume 10, Issue 1-2 p. 125-133 Resolution of topologically chiral molecular objects Jean-Claude Chambron, Jean-Claude Chambron Laboratoire de Chimie Organo-Minérale, URA 422 du CNRS, Université Louis Pasteur, Institut Le Bel, Strasbourg, FranceSearch for more papers by this authorChristiane Dietrich-Buchecker, Christiane Dietrich-Buchecker Laboratoire de Chimie Organo-Minérale, URA 422 du CNRS, Université Louis Pasteur, Institut Le Bel, Strasbourg, FranceSearch for more papers by this authorGwénaël Rapenne, Gwénaël Rapenne Laboratoire de Chimie Organo-Minérale, URA 422 du CNRS, Université Louis Pasteur, Institut Le Bel, Strasbourg, FranceSearch for more papers by this authorJean-Pierre Sauvage, Corresponding Author Jean-Pierre Sauvage Laboratoire de Chimie Organo-Minérale, URA 422 du CNRS, Université Louis Pasteur, Institut Le Bel, Strasbourg, FranceLaboratoire de Chimie Organo-Minérale, URA 422 du CNRS, Université Louis Pasteur, Institut Le Bel, 4, rue Blaise Pascal, 67070 Strasbourg, FranceSearch for more papers by this author Jean-Claude Chambron, Jean-Claude Chambron Laboratoire de Chimie Organo-Minérale, URA 422 du CNRS, Université Louis Pasteur, Institut Le Bel, Strasbourg, FranceSearch for more papers by this authorChristiane Dietrich-Buchecker, Christiane Dietrich-Buchecker Laboratoire de Chimie Organo-Minérale, URA 422 du CNRS, Université Louis Pasteur, Institut Le Bel, Strasbourg, FranceSearch for more papers by this authorGwénaël Rapenne, Gwénaël Rapenne Laboratoire de Chimie Organo-Minérale, URA 422 du CNRS, Université Louis Pasteur, Institut Le Bel, Strasbourg, FranceSearch for more papers by this authorJean-Pierre Sauvage, Corresponding Author Jean-Pierre Sauvage Laboratoire de Chimie Organo-Minérale, URA 422 du CNRS, Université Louis Pasteur, Institut Le Bel, Strasbourg, FranceLaboratoire de Chimie Organo-Minérale, URA 422 du CNRS, Université Louis Pasteur, Institut Le Bel, 4, rue Blaise Pascal, 67070 Strasbourg, FranceSearch for more papers by this author First published: 19 January 1999 https://doi.org/10.1002/chir.20Citations: 30AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat Abstract The enantiomers of topologically chiral molecular objects cannot be interconverted by a continuous deformation. It must be noted that this behavior is opposite to that of molecules showing classical or Euclidian chirality. Interlocked oriented rings and the trefoil knot are prototypical topologically chiral objects. We have been designing a transition-metal templated route to the corresponding real molecules (i.e., [2]-catenanes and molecular knots) using copper(I) as the template and 2,9-diphenyl-1,10-phenanthroline (dpp) based ligands. The precursor to the catenane species was a tetrahedral Cu(dpp)2+ complex in which the two ligands fit in around Cu(I), thereby allowing the interlocking process. In the case of the knot, the precursor was a double-stranded helical complex in which two bis-phenanthroline ligands wrap around two Cu(I) ions. The compounds were obtained as racemates and were resolved as their Cu(I) complexes either by HPLC on chiral stationary phases or by diastereoselective crystallization. For the trefoil knot (K · 2Cu+), the latter method proved to be the most efficient. It took advantage of the dicationic nature of the species to be resolved. The original triflate anion was exchanged by an optically pure anion (S)-(+)-1,1′-binaphthyl-2,2′-diyl phosphate ((+)-BNP-) and the diastereomer (+)-K · 2Cu+ · 2(+)BNP- was selectively crystallized in a mixture of nitromethane and benzene. Removal of the Cu(I) ions by treatment with cyanide afforded an enantiomerically pure molecular knot (K), showing an optical rotatory power close to +2,000° · mol-1 · L · dm-1. Chirality 10:125–133, 1998. © 1998 Wiley-Liss,Inc. Citing Literature Volume10, Issue1-21998Pages 125-133 RelatedInformation