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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2008 - Issue 2
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Original Articles

Concise Synthesis of Dimethyl (2-Oxopropyl)phosphonate and Homologation of Aldehydes to Alkynes in a Tandem Process

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Pages 299-310 | Received 09 May 2008, Published online: 22 Dec 2008

REFERENCES

  • Patai , S. (Ed.). The Chemistry of the Carbon-Carbon Triple Bond ; Wiley : New York , 1978 .
  • Diederich , F. ; Stang , P. J. ; Tykwinski , R. R. (Eds.). Acetylene Chemistry ; Wiley : New York , 2004 .
  • Grubbs , R. H. (Ed.). Handbook of Metathesis ; Wiley : New York , 2003 .
  • (a) Reddy , G. S. ; Tserng , K. Y. Calcitroic acid, end product of renal metabolism of 1,25-dihydroxyvitamin D3 through the C-24 oxidation pathway . Biochem. 1989 , 28 , 1763 – 1769 ; (b) Horst, R. L.; Reinhardt, T. A.; Reddy, G. S. Vitamin D metabolism. In Vitamin D, 2nd ed.; D. Feldman, F. H. Glorieux, and J. W. Pike (Eds.); Academic Press: Amsterdam, 2005; vol. 1, pp. 15–35 .
  • Corey , E. J. ; Fuchs , P. L. A synthetic method for formyl → ethynyl conversion (RCHO → RC≡CH or RC≡CR′) . Tetrahedron Lett. 1972 , 13 , 3769 – 3772 .
  • Ramirez , F. ; Desai , N. B. ; McKelvie , N. A new synthesis of 1,1-dibromoölefins via phosphine-dibromomethylenes: The reaction of triphenylphosphine with carbon tetrabromide . J. Amer. Chem. Soc. 1962 , 84 , 1745 – 1747 .
  • Fürst , M. ; Rück-Braun , K. Safety-catch propargyl-based linker strategy for the immobilization of amines and carboxylic acids in SPOS . Synlett. 2002 , 12 , 1991 – 1994 .
  • Bestmann , H. J. ; Frey , H. Reactions with phosphinealkylenes, 39: New methods for the preparation of 1-bromoacetylenes and aromatic and conjugated enynes . Liebigs Ann. Chem. 1980 , 2061 – 2071 .
  • Wang , Z. ; Campagna , S. ; Yang , K. ; Xu , G. ; Pierce , M. E. ; Fortunak , J. M. ; Confalone , P. N. A practical preparation of terminal alkynes from aldehydes . J. Org. Chem. 2000 , 65 , 1889 – 1891 .
  • (a) Corey , E. J. ; Achiwa , K. ; Katzenellenbogen , J. A. Total synthesis of dl-sirenin . J. Am. Chem. Soc. 1969 , 91 , 4318 – 4320 ; (b) Corey , E. J. ; Ruden , R. A. Stereoselective methods for the synthesis of terminal cis and trans enyne units . Tetrahedron Lett. 1973 , 14 , 1495 – 1499 ; (c) Hengartner , U. ; Bernhard , K. ; Meyer , K. ; Englert , G. ; Glinz , E. Synthesis, isolation, and NMR-spectroscopic characterization of fourteen (Z)-isomers of lycopene and of some acetylenic didehydro- and tetradehydrolycopenes . Helv. Chim. Acta 1992 , 75 , 1848 – 1865 ; (d) Charoenying , P. ; Davies , D. H. ; McKerrecher , D. ; Taylor , R. J. K. A new stereocontrolled, pyrylium-based route to conjugated dienynes: The first synthesis of carduusyne A . Tetrahedron Lett. 1996 , 37 , 1913 – 1916 .
  • Michel , P. ; Gennet , D. ; Rassat , A. A one-pot procedure for the synthesis of alkynes and bromoalkynes from aldehydes . Tetrahedron Lett. 1996 , 40 , 8575 – 8578 .
  • Carran , J. ; Waschbüsch , R. ; Marinetti , A. ; Savignac , P. An improved synthesis of dichloroalkylphosphonates, chloroalkynes, and terminal alkynes via diethyl dichloromethylphosphonate. Synthesis 1996, 12, 1494–1498.
  • (a) Colvin , E. W. ; Hamill , B. J. A simple procedure for the elaboration of carbonyl compounds into homologous alkynes . J. Chem. Soc. Perkin Trans. 1 1977 , 869 – 874 ; (b) Colvin , E. W. ; Hamill , B. J. One-step conversion of carbonyl compounds into acetylenes . J. Chem. Soc., Chem. Commun. 1973 , 151 – 152 .
  • Illa , O. ; Bagan , X. ; Cazorla , A. M. ; Lyon , C. ; Baceiredo , A. ; Branchadell , V. ; Ortuno , R. M. Reaction of C-silylated α-diazophosphines as nucleophiles toward carbonyl compounds: A mechanistic study and application to the synthesis of alkynes and α-hydroxyphosphonamides . J. Org. Chem. 2006 , 71 , 5320 – 5327 .
  • (a) Miwa , K. ; Shioiri , T. ; Aoyama , T. Extension of the Colvin rearrangement using trimethylsilyldiazomethane: A new synthesis of alkynes . Synlett 1994 , 107 – 108 ; (b) Ito , Y. ; Aoyama , T. ; Shioiri , T. A new preparation of benzofurans utilizing trimethylsilyldiazomethane . Synlett 1997 , 10 , 1163 – 1164 .
  • Regitz , M. ; Liedhegener , A. ; Eckstein , U. ; Martin , M. ; Anschuetz , W. Diazo compounds and azides, XIII: Mercuric and silver derivatives from diphenylphosphinyl- and diethylphosphonodiazomethane . Liebigs Ann. Chem. 1971 , 748 , 207 – 210 .
  • Seyferth , D. ; Marmor , R. S. ; Hilbert , P. Reactions of dimethylphosphono-substituted diazoalkanes: (MeO)2P(O)CR transfer to olefins and 1,3-dipolar additions of (MeO)2P(O)C(N2)R . J. Org. Chem. 1971 , 36 , 1379 – 1386 .
  • Brown , D. G. ; Velthuisen , E. J. ; Commerford , J. R. ; Brisbois , R. G. ; Hoye , T. R. A convenient synthesis of dimethyl (diazomethyl)phosphonate (Seyferth/Gilbert reagent) . J. Org. Chem. 1996 , 61 , 2540 – 2541 .
  • Gilbert , J. C. ; Weerasooriya , U. Diazoethenes: Their attempted synthesis from aldehydes and aromatic ketones by way of the Horner–Emmons modification of the Wittig reaction: A facile synthesis of alkynes . J. Org. Chem. 1982 , 47 , 1837 – 1845 .
  • Müller , S. ; Liepold , B. ; Roth , G. J. ; Bestmann , H. J. An improved one-pot procedure for the synthesis of alkynes from aldehydes . Synlett 1996 , 521 – 522 .
  • Meffre , P. ; Hermann , S. ; Durand , P. ; Reginato , G. ; Riu , A. Practical one-step synthesis of ethynylglycine synthon from Garner's aldehyde . Tetrahedron 2002 , 58 , 5159 – 5162 .
  • Roth , G. J. ; Liepold , B. ; Müller , S. G. ; Bestmann , H. J. Further improvements of the synthesis of alkynes from aldehydes . Synthesis 2004 , 59 – 61 .
  • Ohira , S. Methanolysis of dimethyl (1-diazo-2-oxopropyl)phosphonate: Generation of dimethyl (diazomethyl)phosphonate and reaction with carbonyl compounds . Synth. Commun. 1989 , 19 , 561 – 564 .
  • (a) Barrett , A. G. M. ; Hopkins , B. T. ; Love , A. C. ; Tedeschi , L. Parallel synthesis of terminal alkynes using a ROMPgel-supported ethyl 1-diazo-2-oxopropylphosphonate . Org. Lett. 2004 , 6 , 835 – 837 ; (b) For a review of ROMP polymerization, see Harned , A. M. ; Zhang , M. ; Vedantham , P. ; Mukherjee , S. ; Herpel , R. H. ; Flynn , D. L. ; Hanson , P. R. Aldrichimica Acta 2005 , 38 , 3 – 16 .
  • Taber , D. F. ; Ruckle , Jr. , R. E. ; Hennessy , M. J. Mesyl azide: A superior reagent for diazo transfer. J. Org. Chem. 1986, 51, 4077–4078.
  • Lee , J. C. ; Yuk , J. Y. An improved and efficient method for diazo transfer reaction of active methylene compounds . Synth. Commun. 1995 , 25 , 1511 – 1515 .
  • (a) Inokuchi , T. ; Matsumoto , S. ; Nishiyama , T. ; Torii , S. A selective and efficient method for alcohol oxidations mediated by N-oxoammonium salts in combination with sodium bromite . J. Org. Chem. 1990 , 55 , 462 – 466 ; (b) Siedlecka , R. ; Skarzewski , J. ; Mlochowski , J. Selective oxidation of primary hydroxy groups in prinary-secondary diols . Tetrahedron Lett. 1990 , 31 , 2177 – 2180 ; (c) Einhorn , J. ; Einhorn , C. ; Ratajczak , F. ; Pierre , J.-L. Efficient and highly selective oxidation of primary alcohols to aldehydes by N-chlorosuccinimide mediated by oxoammonium salts . J. Org. Chem. 1996 , 61 , 7452 – 7454 .
  • Corbel , B. ; L'Hostis-Kervella , I. ; Haelters , J.-P. On a safe and practical method fort he preparation of β-keto phosphonates . Synth. Commun. 1996 , 26 , 2561 – 2568 .
  • Khabnadideh , S. ; Didier Pez , D. ; Musso , A. ; Brun , R. ; Ruiz Pérez , L. M. ; González-Pacanowska , D. ; Gilbert , I. H. Design, synthesis, and evaluation of 2,4-diaminoquinazolines as inhibitors of trypanosomal and leishmanial dihydrofolate reductase . Bioorg. Med. Chem. 2005 , 13 , 2637 – 2649 .
  • Lythgoe , B. ; Roberts , D. A. ; Waterhouse , I. Calciferol and its relatives, part 20: A synthesis of Windaus and Grundmann's C19 ketone . J. Chem. Soc. Perkin Trans. 1 1977 , 2608 – 2612 .
  • Bouillon , R. ; De Clerq , P. J. ; Pirson , P. ; Vandewalle , M. ; Baudrihaye , M. Preparation of epoxidized vitamin D derivatives as drugs. WO Patent, 9221695 , 1992 .
  • Barbier , P. ; Bauer , F. ; Mohr , P. ; Muller , M. ; Pirson , W. Preparation of arylsecocholadiene derivatives with vitamin D activity. WO Patent, 9847866 , 1998 .
  • Manchand , P. S. ; Uskokovic , M. Preparation of 1,3-dihydroxy-20,20-dialkyl-vitamin D3 analogs for pharmaceutical use. WO Patent, 9912894 , 1999 .

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