A remarkable temperature effect in the desymmetrisation of bridged meso-tricyclic succinic anhydrides with chiral oxazolidin-2-ones

A temperature dependent reversal of diastereoselectivity was observed in the desymmetrisation of bridged meso-tricyclic succinic anhydrides with lithiated chiral oxazolidin-2-ones that appears to be kinetically driven at low temperature while the reversibility of the reaction sets in at higher temperatures and thermodynamics governs the reaction outcome.

[1]  R. Manzano,et al.  Synthesis of both enantiomers of hemiesters by enantioselective methanolysis of meso cyclic anhydrides catalyzed by alpha-amino acid-derived chiral thioureas. , 2010, The Journal of organic chemistry.

[2]  M. Bartók.  Unexpected inversions in asymmetric reactions: reactions with chiral metal complexes, chiral organocatalysts, and heterogeneous chiral catalysts. , 2010, Chemical reviews.

[3]  J. Mulzer,et al.  Remarkable temperature effect on intramolecular [3+2] cyclization , 2009 .

[4]  P. Carter,et al.  Enantioselective synthesis of benzyl (1S,2R,4R)-4-(tert-butoxycarbonylamino)-2-(hydroxymethyl)cyclohexylcarbamate using an iodolactamization as the key step. , 2009, The Journal of organic chemistry.

[5]  Z. Hameršak,et al.  Inversion of enantioselectivity in quinine-mediated desymmetrization of glutaric meso-anhydrides , 2009 .

[6]  J. Mowat,et al.  Inverse temperature dependence in the diastereoselective addition of Grignard reagents to a tetrahydrofurfural. , 2009, Organic letters.

[7]  X. Hao,et al.  Structural elucidation of daphniacetal A, a new oxa-cage compound isolated from Daphniphyllum macropodum Miq. , 2009 .

[8]  A. C. Evans,et al.  Highly diastereoselective desymmetrisation of cyclic meso-anhydrides and derivatisation for use in natural product synthesis. , 2009, Organic and biomolecular chemistry.

[9]  S. Ghosh,et al.  An efficient asymmetric desymmetrization of prochiral glutaric anhydrides with SuperQuat chiral oxazolidin-2-ones , 2008 .

[10]  C. Song,et al.  A highly reactive and enantioselective bifunctional organocatalyst for the methanolytic desymmetrization of cyclic anhydrides: prevention of catalyst aggregation. , 2008, Angewandte Chemie.

[11]  V. Puranik,et al.  Use of enantiomerically pure 7-azabicyclo[2.2.1]heptan-2-ol as a chiral template for the synthesis of aminocyclitols. , 2008, Organic letters.

[12]  S. Gellman,et al.  Diacid linkers that promote parallel beta-sheet secondary structure in water. , 2008, Journal of the American Chemical Society.

[13]  C. Song,et al.  Bifunctional organocatalyst for methanolytic desymmetrization of cyclic anhydrides: increasing enantioselectivity by catalyst dilution. , 2008, Chemical communications.

[14]  C. Bolm,et al.  Stereoselective anhydride openings. , 2007, Chemical reviews.

[15]  G. Lin,et al.  Room-temperature highly diastereoselective Zn-mediated allylation of chiral N-tert-butanesulfinyl imines: remarkable reaction condition controlled stereoselectivity reversal. , 2006, Organic letters.

[16]  Jieping Zhu,et al.  Synthesis of chiral vicinal diamines by highly diastereoselective three-component phenolic Mannich reaction: temperature-dependent stereodivergency. , 2005, Organic letters.

[17]  J. Choi,et al.  Heterogeneous organocatalysis for the asymmetric desymmetrization of meso-cyclic anhydrides using silica gel-supported bis-cinchona alkaloids , 2004 .

[18]  Jian Zhou,et al.  Diastereoselectivity-switchable and highly enantioselective 1,3-dipolar cycloaddition of nitrones to alkylidene malonates. , 2004, Organic letters.

[19]  J. Choi,et al.  Silica gel-supported bis-cinchona alkaloid: a chiral catalyst for the heterogeneous asymmetric desymmetrization of meso-cyclic anhydrides , 2004 .

[20]  B. Trost,et al.  Direct catalytic asymmetric aldol additions of methyl ynones. Spontaneous reversal in the sense of enantioinduction. , 2004, Journal of the American Chemical Society.

[21]  L. Deng,et al.  Asymmetric alcoholysis of cyclic anhydrides. , 2003, Chemical reviews.

[22]  C. Tanyeli,et al.  The first enantioselective synthesis of chiral norbornane-type 1,4-diamine ligand , 2003 .

[23]  A. Quintavalla,et al.  Solvent and Temperature Effects on Diastereofacial Selectivity: Amines as Co‐Solvents in n‐Butyllithium Addition to α‐Chiral Aldehydes , 2003 .

[24]  M. Sibi,et al.  Temperature dependent reversal of stereochemistry in enantioselective conjugate amine additions , 2002 .

[25]  P. Seneci,et al.  Stereoselective synthesis of conformationally constrained cyclohexanediols: a set of molecular scaffolds for the synthesis of glycomimetics. , 2001, The Journal of organic chemistry.

[26]  A. Spivey,et al.  Catalysis of the Asymmetric Desymmetrization of Cyclic Anhydrides by Nucleophilic Ring-Opening with Alcohols. , 2001, Angewandte Chemie.

[27]  M. North,et al.  Synthesis of Enantiomerically Pure, All Syn, Tetra and Pentasubstituted Cyclopentanes by the Desymmetrisation of Endo-Norborn-5-ene-2,3-Dicarboxylic Anhydrides , 2000 .

[28]  C. Bolm,et al.  Practical and highly enantioselective ring opening of cyclic meso-anhydrides mediated by cinchona alkaloids. , 2000, The Journal of organic chemistry.

[29]  L. Deng,et al.  A Highly Enantioselective Catalytic Desymmetrization of Cyclic Anhydrides with Modified Cinchona Alkaloids , 2000 .

[30]  E. Carreira,et al.  Enantioselective Synthesis of the Cyclopentyl Core of the Axinellamines , 2000 .

[31]  P. Galletti,et al.  Temperature and solvent effects in facial diastereoselectivity of nucleophilic addition: entropic and enthalpic contribution , 2010 .

[32]  D. Hibbs,et al.  Synthesis of Enantio- and Diastereomerically Pure, Tetra- and Penta-Substituted Cyclopentanes by the Desymmetrization of endo-Norborn-5-ene-2,3-dicarboxylic Anhydrides. , 1999, The Journal of organic chemistry.

[33]  C. Bolm,et al.  Simple and Highly Enantioselective Nonenzymatic Ring Opening of Cyclic Prochiral Anhydrides , 1999 .

[34]  R. Verma,et al.  Desymmetrization of 3-dimethyl(phenyl)silyl glutaric anhydride with Evans’ oxazolidinone: an application to stereocontrolled synthesis of the antifungal agent (+)-preussin , 1999 .

[35]  P. Galletti,et al.  Reversal Diastereofacial Selectivity in then-Butyllithium Addition toO-ProtectedN-Trimethylsilylimines of (2S)-Lactal: Enthalpic versus Entropic Contributions , 1999 .

[36]  R. Verma,et al.  Desymmetrization of prochiral anhydrides with Evans’ oxazolidinones: an efficient route to homochiral glutaric and adipic acid derivatives , 1999 .

[37]  D. Seebach,et al.  A Useful Modification of the Evans Auxiliary: 4‐Isopropyl‐5,5‐diphenyloxazolidin‐2‐one , 1998 .

[38]  D. Seebach,et al.  Highly Enantioselective Ring Opening of Cyclic Meso-Anhydrides to Isopropyl Hemiesters with Ti−TADDOLates: An Alternative to Hydrolytic Enzymes? , 1998 .

[39]  N. Hashimoto,et al.  Reversal of stereoselection in diastereodivergence of meso-dicarboxylic anhydrides , 1996 .

[40]  D. Ager,et al.  1,2-Amino Alcohols and Their Heterocyclic Derivatives as Chiral Auxiliaries in Asymmetric Synthesis. , 1996, Chemical reviews.

[41]  D. Seebach,et al.  Highly Enantioselective Opening of Cyclic meso‐Anhydrides to Isopropyl Hemiesters with Diisopropoxytitanium TADDOLates , 1995 .

[42]  M. North,et al.  Asymmetric Desymmetrisation of Meso-Norbornene Anhydrides Utilising Methyl Prolinate as a Chiral Reagent , 1995 .

[43]  J. Gilmore,et al.  Asymmetric Synthesis of a Lignan Lactone from a meso Anhydride. , 1995 .

[44]  S. Davies,et al.  4-Substituted-5,5-dimethyl oxazolidin-2-ones as effective chiral auxiliaries for enolate alkylations and Michael additions , 1995 .

[45]  T. Kunieda,et al.  Highly effective diastereodifferentiation of Meso-dicarboxylic anhydrides using sterically congested chiral N-sulfonylaminoalcohols , 1995 .

[46]  T. Konoike,et al.  Practical Synthesis of Chiral Synthons for the Preparation of HMG-CoA Reductase Inhibitors , 1994 .

[47]  D. Kronenthal,et al.  A novel and highly efficient desymmetrization of a meso-anhydride by a chiral grignard reagent , 1993 .

[48]  K. B. Sharpless,et al.  Temperature Effects in Asymmetric Dihydroxylation: Evidence for a Stepwise Mechanism , 1993 .

[49]  M. Shimizu,et al.  Enantioselective Esterification of Cyclic Dicarboxylic Anhydrides Using Chiral Amino Alcohols as Auxiliaries , 1993 .

[50]  C. Heathcock,et al.  Prochiral recognition in the reaction of 3-substituted glutaric anhydrides with chiral secondary alcohols , 1993 .

[51]  M. Narisada,et al.  Highly effective and practical enantioselective synthesis of half-esters of bicyclo[2.2.1]heptanedicarboxylic acid , 1991 .

[52]  N. Hoffmann,et al.  The Isoinversion Principle—a General Model of Chemical Selectivity , 1991 .

[53]  R. Aitken,et al.  Catalytic asymmetric ring-opening of bridged tricyclic anhydrides , 1990 .

[54]  M. Ohshima,et al.  Highly Efficient Asymmetric Esterification of Cyclic meso-Dicarboxylic Anhydrides Catalyzed by Diphenylboryl Triflate , 1987 .

[55]  Davidr . Evans,et al.  Asymmetric glycine enolate aldol reactions: synthesis of cyclosporin's unusual amino acid, MeBmt , 1986 .