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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 18
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Original Articles

Enantiomerically Enriched Bicyclic Hydroxamic Acids in One Step from α-Aminohydroxamic Acids and Keto Acids via Cyclocondensation

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Pages 2484-2492 | Received 03 Jul 2012, Published online: 03 Jun 2013

REFERENCES

  • Bapat , J. B. ; Black , D. St. C. ; Brown , R. F. C. Cyclic hydroxamic acids . Adv. Heterocycl. Chem. 1969 , 10 , 199 – 240 .
  • Jourden , J. L. M. ; Cohen , S. M. Enzymatic activation of a matrix metalloproteinase inhibitor . Chem. Commun. 2010 , 46 , 1241 – 1243 .
  • Schlemminger , I. ; Mole , D. R. ; McNeill , L. A. ; Dhanda , A. ; Hewitson , K. S. ; Tian , Y.-M. ; Ratcliffe , P. J. ; Pugh , C. W. ; Schofield , C. J. Analogues of dealanylalahopcin are inhibitors of human HIF prolyl hydroxylases . Bioorg. Med. Chem. Lett. 2003 , 13 , 1451 – 1454 .
  • (a) Brondel , N. ; Renoux , B. ; Gesson , J.-P. New strategy for the synthesis of phosphatase inhibitors TMC-69–6H and analogs . Tetrahedron Lett. 2006 , 47 , 9305 – 9308 ; (b) Kohno , J. ; Hirano , N. ; Sugawara , K. ; Nishio , M. ; Hashiyama , T. ; Nakanishi , N. ; Komatsubara , S. Structure of TMC-69, a new antitumor antibiotic from Chrysosporium sp. TC 1068 . Tetrahedron 2001 , 57 , 1731 – 1735 .
  • Galatsis , P. ; Caprathe , B. ; Downing , D. ; Gilmore , J. ; Harter , W. ; Hays , S. ; Kostlan , C. ; Linn , K. ; Lunney , E. ; Para , K. ; Thomas , A. ; Warmus , J. ; Allen , H. ; Brady , K. ; Talanian , R. ; Walker , N. Inhibition of interleukin-1β converting enzyme (ICE or caspase 1) by aspartyl acyloxyalkyl ketones and aspartyl amidooxyalkyl ketones . Bioorg. Med. Chem. Lett. 2010 , 20 , 5089 – 5094 .
  • Johnson , T. W. ; Tanis , S. P. ; Butler , S. L. ; Dalvie , D. ; DeLisle , D. M. ; Dress , K. R. ; Flahive , E. J. ; Hu , Q. ; Kuehler , J. E. ; Kuki , A. , Liu , W. ; McClellan , G. A. ; Peng , Q. ; Plewe , M. B. ; Richardson , P. F. ; Smith , G. L. ; Solowiej , J. ; Tran , K. T. ; Wang , H. ; Yu , X. ; Zhang , J. ; Zhu , H. Design and synthesis of novel N-hydroxy-dihydronaphthyridinones as potent and orally bioavailable HIV-1 integrase inhibitors . J. Med. Chem. 2011 , 54 , 3393 – 3417 .
  • (a) Pinard , E. ; Burner , S. ; Cueni , P. ; Montavon , F. ; Zimmerli , D. A short and efficient synthesis of the NMDA glycine site antagonist: (3R,4R)-3-amino-1-hydroxy-4-methyl pyrrolidin-2-one (L-687,414) . Tetrahedron Lett. 2008 , 49 , 6079 – 6080 ; (b) Leeson , P. D. ; Williams , B. J. ; Baker , R. ; Ladduwahetty , T. ; Moore , K. W. ; Rowley , M. Effects of five-membered ring conformation on bioreceptor recognition: identification of 3R-amino-1-hydroxy-4R-methylpyrrolidin-2-one (L-687,414) as a potent glycine/N-methyl-D-aspartate receptor antagonist . J. Chem. Soc., Chem. Commun. 1990 , 22 , 1578 – 1580 .
  • Mesaik , M. A. ; Khan , K. M. ; Rahat , S. ; Zia-Ullah ; Choudhary , M. I. ; Murad , S. ; Abdullah , N. R. ; Ismail , Z. ; Atta-ur-Rahman ; Ahmad , A. ; Siddiqui , R. A. Immunomodulatory properties of synthetic imidazolone derivatives. Lett. Drug Design Discovery 2005, 2, 490–496.
  • (a) Jones , I. L. ; Moore , F. K. ; Chai , C. L. L. Total synthesis of (±)-cordypyridones A and B and related epimers . Org. Lett. 2009 , 11 , 5526 – 5529 ; (b) Isaka , M. ; Tanticharoen , M. ; Kongsaeree , P. ; Thebtaranonth , Y. Structures of cordypyridones A–D, antimalarial N-hydroxy- and N-methoxy-2-pyridones from the insect pathogenic fungus Cordyceps nipponica . J. Org. Chem. 2001 , 66 , 4803 – 4808 .
  • (a) Vystorop , I. V. ; Aliev , Z. G. ; Andreeva , N. Y. ; Atovmyan , L. O. ; Fedorov , B. S. Reaction of DL-2-aminopropiohydroxamic acid with acetone: Selective synthesis of 3-hydroxy-2,2,5-trimethylimidazolidin-4-one . Russ. Chem. Bull., Int. Ed. 2000 , 49 , 182 – 183 ; (b) Vystorop , I. V. ; Konovalova , N. P. ; Nelyubina , Y. V. ; Varfolomeev , V. N. ; Fedorov , B. S. ; Sashenkova , T. E. ; Berseneva , E. N. ; Lyssenko , K. A. ; Kostyanovsky , R. G. Cyclic hydroxamic acids derived from α-amino acids 1: Regioselective synthesis, structure, NO-donor, and antimetastatic activities of spirobicyclic hydroxamic acids derived from glycine and DL-alanine . Russ. Chem. Bull., Int. Ed. 2010 , 59 , 127 – 135 ; (c) Vystorop , I. V. ; Nelyubina , Y. V. ; Voznesensky , V. N. ; Sun , W.-H. ; Lodygina , V. P. ; Lyssenko , K. A. ; Kostyanovsky , R. G. General regioselective synthesis and crystal structure of racemic 5-substituted 2,2-dimethyl-3-hydroxyimidazolidin-4-ones . Mendeleev Commun. 2010 , 20 , 106 – 108 ; (d) Vystorop , I. V. ; Lyssenko , K. A. ; Voznesensky , V. N. ; Lodygina , V. P. ; Kostyanovsky , R. G. General regioselective synthesis of 2,2-disubstituted 3-hydroxyimidazolidin-4-ones . Mendeleev Commun. 2002 , 193 – 196 ; (e) Vystorop , I. V. ; Lyssenko , K. A. ; Kostyanovsky , R. G. 3-Hydroxy-2,2-dimethylimidazolidin-4-one: the regioselective synthesis and chiral crystallization . Mendeleev Commun. 2002 , 85 – 87 ; (f) Marson , C. M. ; Pucci , S. Three-component condensations of aldehydes with N-methoxycarboxamides . Tetrahedron Lett. 2004 , 45 , 9007 – 9010 ; (g) Cordi , A. ; Lacoste , J.-M. ; Audinot , V. ; Millan , M. Design, synthesis, and structure-activity relationships of novel strychnine-insensitive glycine receptor ligands . Bioorg. Med. Chem. Lett. 1999 , 9 , 1409 – 1414 ; (h) Barlaam , B. ; Koza , P. ; Berriot , J. Solid-phase synthesis of hydroxamic acid based TNF-α convertase inhibitors . Tetrahedron 1999 , 55 , 7221 – 7232 ; (i) Harmon , R. E. ; Rizzo , V. L. ; Gupta , S. K. Synthesis of 3-hydroxy-4-imidazolidinones (1a,b) . J. Heterocycl. Chem. 1970 , 7 , 439 – 442 .
  • (a) Bolm , C. Vanadium-catalyzed asymmetric oxidations. Coord. Chem. Rev. 2003, 237, 245–256; (b) Sharpless , K. B. ; Verhoeven , T. R. Metal-catalyzed, highly selective oxygenations of olefins and acetylenes with tert-butyl hydroperoxide: Practical considerations and mechanisms. Aldrichim. Acta 1979, 12, 63–74 (c) Michaelson , R. C. ; Palermo , R. E. ; Sharpless , K. B. Chiral hydroxamic acids as ligands in the vanadium catalyzed asymmetric epoxidation of allylic alcohols by tert-butyl hydroperoxides. J. Am. Chem. Soc. 1977, 99, 1990–1992; (d) Li , Z. ; Yamamoto , H. Zirconium(IV)- and hafnium(IV)-catalyzed highly enantioselective epoxidation of homoallylic and bishomoallylic alcohols. J. Am. Chem. Soc. 2010, 132, 7878–7880; (e) Malkov , A. V. ; Czemerys , L. ; Malyshev , D. A. Vanadium-catalyzed asymmetric epoxidation of allylic alcohols in water. J. Org. Chem. 2009, 74, 3350–3355; (f) Li , Z. ; Zhang , W. ; Yamamoto , H. Vanadium-catalyzed enantioselective desymmetrization of meso secondary allylic alcohols and homoallylic alcohols. Angew. Chem., Int. Ed. 2008, 47, 7520–7522; (g) Zhang , W. ; Yamamoto , H. Vanadium-catalyzed asymmetric epoxidation of homoallylic alcohols. J. Am. Chem. Soc. 2007, 129, 286–287; (h) Bourhani , Z. ; Malkov , A. V. Vanadium-catalyzed asymmetric epoxidation: Proline-derived hydroxamic acids revisited. Synlett 2006, 3525–3528; (i) Malkov , A. V. ; Bourhani , Z. ; Kočovsky , P. Amino acid-derived hydroxamic acids as chiral ligands in the vanadium catalyzed epoxidation. Org. Biomol. Chem. 2005, 3, 3194–3200; (j) Bourhani , Z. ; Malkov , A. V. Ligand-accelerated vanadium-catalyzed epoxidation in water. Chem. Commun. 2005, 4592–4594; (k) Zhang , W. ; Basak , A. ; Kosugi , Y. ; Hoshino , Y. ; Yamamoto , H. Enantioselective epoxidation of allylic alcohols by a chiral complex of vanadium: An effective controller system and a rational mechanistic model. Angew. Chem., Int. Ed. 2005, 44, 4389–4391; (l) Makita , N. ; Hoshino , Y. ; Yamamoto , H. Asymmetric epoxidation of homoallylic alcohols and application in a concise total synthesis of (−)-α-bisabolol and (−)-8-epi-α-bisabolol. Angew. Chem., Int. Ed. 2003, 42, 941–943; (m) Wu , H.-L. ; Uang , B.-J. Asymmetric epoxidation of allylic alcohols catalyzed by new chiral vanadium(V) complexes. Tetrahedron: Asymmetry 2002, 13, 2625–2628.
  • Olivares-Romero , J. L. ; Li , Z. ; Yamamoto , H. Hf(IV)-catalyzed enantioselective epoxidation of N-alkenyl sulfonamides and N-tosyl imines . J. Am. Chem. Soc. 2012 , 134 , 5440 – 5443 .
  • Barlan , A. U. ; Basak , A. ; Yamamoto , H. Enantioselective oxidation of olefins catalyzed by a chiral bishydroxamic acid complex of molybdenum . Angew. Chem., Int. Ed. 2006 , 45 , 5849 – 5852 .
  • (a) Basak , A. ; Barlan , A. U. ; Yamamoto , H. Catalytic enantioselective oxidation of sulfides and disulfides by a chiral complex of bis-hydroxamic acid and molybdenum . Tetrahedron: Asymmetry 2006 , 17 , 508 – 511 ; (b) Barlan , A. U. ; Zhang , W. ; Yamamoto , H. Development and application of versatile bis-hydroxamic acids for catalytic asymmetric oxidation . Tetrahedron 2007 , 63 , 6075 – 6087 .
  • (a) Ahlford , K. ; Adolfsson , H. Amino acid–derived amides and hydroxamic acids as ligands for asymmetric transfer hydrogenation in aqueous media . Catal. Commun. 2011 , 12 , 1118 – 1121 ; (b) Ahlford , K. ; Zaitsev , A. B. ; Ekström , J. ; Adolfsson , H. A simple and efficient catalyst system for the asymmetric transfer hydrogenation of ketones . Synlett 2007 , 2541 – 2544 .
  • Charbonnel , Y. ; Barrans , J. Action of aldehydes on 2-aminohydroxamic acids . Compt. Rend. 1966 , 263C , 824 – 827 .
  • (a) Verardo , G. ; Geatti , P. ; Merli , M. ; Castellarin , E. E. Synthesis of 3-substituted dihydro-1-phenylamino-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones from α-amino acid phenylhydrazides and levulinic acid . Eur. J. Org. Chem. 2004 , 2833 – 2839 ; (b) Verardo , G. ; Geatti , P. ; Martinuzzi , P. ; Merli , M. ; Toniutti , N. Condensation reaction between α-amino acid phenylhydrazides and carbonyl compounds . Eur. J. Org. Chem. 2003 , 3840 – 3849 .
  • Smissman , E. E. ; Warner , V. D. Specificity in enzyme inhibition, 2: α-Aminohydroxamic acids as inhibitors of histidine decarboxylase and 3,4-dihydroxyphenylalanine decarboxylase . J. Med. Chem. 1972 , 15 , 681 – 682 .
  • (a) Lázár , L. ; Fülöp , F. Recent developments in the ring-chain tautomerism of 1,3-heterocycles . Eur. J. Org. Chem. 2003 , 3025 – 3042 ; (b) Groaning , M. D. ; Meyers , A. I. Chiral non-racemic bicyclic lactams: Auxiliary-based asymmetric reactions . Tetrahedron 2000 , 56 , 9843 – 9873 .
  • Katritzky , A. R. ; Xu , Y.-J. ; He , H.-Y. ; Steel , P. J. Stereoselective syntheses of 1H-imidazo[2,1-a]isoindole-2,5(3H,9bH)-diones . J. Chem. Soc., Perkin Trans. 1 2001 , 1767 – 1770 .

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