Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 21
186
Views
4
CrossRef citations to date
0
Altmetric
Original Articles

Studies on the Selective Reduction of the Amide Link of Acyclic and Macrocyclic Amidoketals: Unexpected Cleavage and trans‐Acetalization with Red‐Al®

&
Pages 3729-3740 | Received 07 Mar 2007, Published online: 19 Oct 2007

References

  • Brown , H. C. and Heim , P. 1973 . Selective reductions, XVIII: The fast reaction of primary, secondary, and tertiary amides with diborane: A simple convenient procedure for the conversion of amides to the corresponding amines . J. Org. Chem. , 38 : 912 – 916 . and references cited therein
  • Lane , C. F. 1977 . Selective reductions using borane complexes . Aldrichimica Acta , 10 : 41 – 51 . and references cited therein
  • Lane , C. F. 1976 . Reduction of organic compounds with diborane . Chem. Rev. , 76 : 773 – 799 . and references cited therein
  • Brown , H. C. , Choi , Y. M. and Narasimhan , S. 1982 . Selective reductions, 29: A simple technique to achieve an enhanced rate of reduction of representative organic compounds by borane‐dimethyl sulfide . J. Org. Chem. , 47 : 3153 – 3163 . and references cited therein
  • Winterfeldt , E. 1975 . Applications of diisobutylaluminium hydride (DIBAH) and triisobutylaluminium (TIBA) as reducing agents in organic synthesis . Synthesis , : 617 – 630 .
  • Agami , C. , Dechoux , L. , Hebbe , S. and Ménard , C. 2004 . Enantioselective synthesis of indolizidine and quinolizidine derivatives from chiral non‐racemic bicyclic lactams . Tetrahedron , 60 : 5433 – 5438 .
  • Paolucci , C. and Mattioli , L. 2001 . Stereoisomeric sugar‐derived indolizines as versatile building blocks: Synthesis of enantiopure di‐ and tetra‐hydroxyindolizidines . J. Org. Chem. , 66 : 4787 – 4794 .
  • Katritzky , A. R. , Belyakov , S. A. , Rachwal , B. and Moutou , J.‐L. 1997 . Lewis acid‐catalyzed additions of (benzotriazol‐1‐yl)diethoxymethane to enol ethers and enamides: New syntheses of β‐alkoxyalkanal and β‐aminoalkanal acetals . J. Org. Chem. , 62 : 700 – 705 .
  • Doedens , R. J. , Meier , G. P. and Overman , L. E. 1988 . Transition‐state geometry of [3,3]‐sigmatropic rearrangements of iminium ions . J. Org. Chem. , 53 : 685 – 690 .
  • Compernolle , F. , Saleh , M.‐A. , Toppet , S. and Hoornaert , G. 1991 . Synthesis of 2,5‐substituted piperidines and their bicyclic piperazine analogues: The 2,7‐substituted octahydro‐2H‐pyrido[1,2‐a]pyrazines . J. Org. Chem. , 56 : 5192 – 5196 .
  • Lescrinier , E. , Pannecouque , C. , Rozenski , J. , Van Aerschot , A. , Kerremans , L. and Herdewijn , P. 1996 . Synthesis of N 6 ‐alkylated adenosine derivatives . Nucleosides Nucleotides , 15 : 1863 – 1869 .
  • Badalassi , F. , Crotti , P. , Favero , L. , Macchia , F. and Pineschi , M. 1997 . Improved stereoselective synthesis of both methyl α‐ and β‐glycosides corresponding to the amino sugar component of the E ring of calicheamicin γ1I and esperamicin A1 . Tetrahedron , 53 : 14369 – 14380 .
  • Albertini , E. , Barco , A. , Benetti , S. , De Risi , C. , Pollini , G. P. and Zanirato , V. 1997 . A unified asymmetric approach to substituted hexahydroazepine and 7‐azabicyclo[2.2.1]heptane ring systems from D(−)‐quinic acid: Application to the formal syntheses of (−)‐balanol and (−)‐epibatidine . Tetrahedron , 53 : 17177 – 17194 .
  • Garcia , C. , Pointud , Y. , Jeminet , G. , Dugat , D. and Beltran , J.‐L. 1998 . Chiral macrocyclic polyethers incorporating a tetraoxaspiro[5.5]undecane or trioxa‐azaspiro[5.5]undecane moiety . Tetrahedron: Asymmetry , 9 : 4253 – 4265 .
  • Hubbs , J. L. and Heathcock , C. H. 1999 . Total synthesis of (±)‐isoschizogamine . Org. Lett. , 1 : 1315 – 1317 .
  • Matzanke , N. , Löwe , W. , Perachon , S. , Sokoloff , P. , Schwartz , J.‐C. and Stark , H. 1999 . Heterocyclic congeners of PD 128,907 with a partially hydrogenated benzomorpholine moiety as potential dopamine D3‐receptor ligands . Eur. J. Med. Chem. , 34 : 791 – 798 .
  • Pansare , S. V. and Ravi , R. G. 1998 . Asymmetric reactions of α‐ketoacid‐derived hemiacetals: Stereoselective synthesis of α‐hydroxy acids . Tetrahedron , 54 : 14549 – 14564 .
  • Meyers , A. I. , Andres , C. J. , Resek , J. E. , Woodall , C. C. , McLaughlin , M. A. , Lee , P. H. and Price , D. A. 1999 . Asymmetric routes to azasugars from chiral bicyclic lactams: Synthesis of 1,4‐dideoxy‐1,4‐imino‐D‐lyxitol; L‐deoxymannojirimycin; rhammo‐1‐deoxynojirimycin and 1‐deoxy‐6‐epicastanospermine . Tetrahedron , 55 : 8931 – 8952 .
  • Bedürftig , S. , Weigl , M. and Wünsch , B. 2001 . (1‐Benzylpiperazin‐2‐yl)methanols: Novel EPC synthesis from (S)‐serine and transformation into ligands for central nervous system receptors . Tetrahedron: Asymmetry , 12 : 1293 – 1302 .
  • Valade , A.‐G. , Dugat , D. , Jeminet , G. , Royer , J. and Husson , H.‐P. 2001 . Structural features in the seven‐membered vs. fourteen‐membered ring cyclization of hydroxyamido ketals derived from β‐amino alcohols . Eur. J. Org. Chem. , 11 : 2041 – 2053 .
  • Dugat , D. , Valade , A.‐G. , Combourieu , B. and Guyot , J. 2005 . Conformational analysis of new 14‐membered ring diketal dilactam macrocycles: Molecular mechanics, liquid and solid state NMR studies . Tetrahedron , 61 : 5641 – 5653 .
  • Pointud , Y. , Valade , A.‐G. , Pointon , C. , Dugat , D. , Jeminet , G. and Beltran , J.‐L. 2003 . Macrocyclic 14‐membered ring diketal dilactams: Evaluation of their divalent cation binding properties . Supramol. Chem. , 15 : 261 – 269 .
  • Muller , F. R. and Handel , H. 1982 . Tetraazamacrocycles lipophiles: Synthèse et application à l'extraction de Cu(II), Cd(II) et Pb(II) . Tetrahedron Lett. , 23 : 2769 – 2772 .
  • Kimura , E. 1992 . Macrocyclic polyamines with intelligent functions . Tetrahedron , 48 : 6175 – 6217 .
  • Guilard , R. , Roux‐Fouillet , B. , Lagrange , G. , Meyer , M. and Bucaille , A. T. 2001 . Polyazacycloalcanes, complexes organométalliques les incorporant comme ligands ainsi que utilisation desdit composés à l'extraction de métaux lourds . Chem. Abstr. , 135 : 70118z PCT Int. Appl. WO 01 46202, 2001
  • Barbette , F. , Rascalou , F. , Chollet , H. , Babouhot , J. L. , Denat , F. and Guilard , R. 2004 . Extraction of uranyl ions from aqueous solutions using silica‐gel‐bound macrocycles for alpha contaminated waste water treatment . Anal. Chim. Acta , 502 : 179 – 187 .
  • Kinneary , J. F. , Albert , J. S. and Burrows , C. J. 1988 . Mechanistic studies of alkene epoxidation catalyzed by nickel(II) cyclam complexes: 18O Labeling and substituent effects . J. Am. Chem. Soc. , 110 : 6124 – 6129 .
  • Dubois , G. , Tripier , R. , Brandès , S. , Denat , F. and Guilard , R. 2002 . Cyclam complexes containing silica gels for dioxygen adsorption . J. Mat. Chem. , 12 : 2255 – 2261 .
  • Liang , X. and Sadler , P. J. 2004 . Cyclam complexes and their applications in medicine . Chem. Soc. Rev. , 33 : 246 – 266 . and references therein
  • Yoon , N. M. and Gyoung , Y. S. 1985 . Reaction of diisobutylaluminium hydride with selected organic compounds containing representative functional groups . J. Org. Chem. , 50 : 2443 – 2450 .
  • Yamashita , M. and Ojima , I. 1983 . Effective route to azetidines from azetidin‐2‐ones using hydroalanes as specific reducing agents . J. Am. Chem. Soc. , 105 : 6339 – 6342 .
  • Cerny , M. , Malek , J. , Capka , M. and Chvalovsky , V. 1969 . Properties of sodium bis‐(2‐methoxyethoxy)aluminium hydride, IV: Reduction of oximes, amides, lactams, imides and nitriles . Collect. Czech. Chem. Commun. , 34 : 1033 – 1041 .
  • Malek , J. and Cerny , M. 1972 . Reduction of organic compounds by alkoxyaluminohydrides . Synthesis , : 217 – 234 .
  • Malek , J. 1989 . Reductions by metal alkoxyaluminum hydrides, part II: Carboxylic acids and derivatives, nitrogen compounds, and sulfur compounds . Org. Synth. , 36 : 289 – 298 .
  • Corey , E. J. , Katzenellenbogen , J. A. and Posner , G. H. 1967 . A new stereospecific synthesis of trisubstituted olefins: Stereospecific synthesis of farnesol . J. Am. Chem. Soc. , 89 : 4245 – 4247 .
  • Pierre , J.‐L. , Handel , H. and Perraud , R. 1975 . Sur le rôle fondamental du cation alcalin dans la réduction des cétones par les hydrures métalliques: Utilisation de coordinats macrocycliques III: Etude de divers groupements fonctionnels réduits par LiAlH4 . Tetrahedron , 31 : 2795 – 2798 . and references cited therein
  • Ashby , E. C. and Boone , J. R. 1976 . Mechanism of lithium aluminium hydride reduction of ketones: Kinetics of reduction of mesityl phenyl ketone . J. Am. Chem. Soc. , 98 : 5524 – 5531 .
  • Wiegers , K. E. and Smith , S. G. 1978 . Kinetics and mechanism of lithium aluminium hydride and lithium alkoxyaluminohydride reduction of ketones in tetrahydrofuran . J. Org. Chem. , 43 : 1126 – 1131 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.