메뉴 건너뛰기




Volumn 39, Issue 2, 2009, Pages 299-310

Concise synthesis of dimethyl (2-oxopropyl)phosphonate and homologation of aldehydes to alkynes in a tandem process

Author keywords

Alcohols; Aldehydes; Alkynes; Homologation; Oxidation

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; ALKYNE; AZIDE; BASE; REAGENT; SOLVENT; TOSYLCHLORAMIDE SODIUM;

EID: 58149127315     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802372566     Document Type: Article
Times cited : (12)

References (42)
  • 2
    • 21244469739 scopus 로고    scopus 로고
    • Diederich, F, Stang, P. J, Tykwinski, R. R, Eds, Wiley: New York
    • Diederich, F.; Stang, P. J.; Tykwinski, R. R. (Eds.). Acetylene Chemistry; Wiley: New York, 2004.
    • (2004) Acetylene Chemistry
  • 3
    • 1442360753 scopus 로고    scopus 로고
    • Grubbs, R. H, Ed, Wiley: New York
    • Grubbs, R. H. (Ed.). Handbook of Metathesis; Wiley: New York, 2003.
    • (2003) Handbook of Metathesis
  • 4
    • 0024574048 scopus 로고
    • Calcitroic acid, end product of renal metabolism of 1,25-dihydroxyvitamin D3 through the C-24 oxidation pathway
    • (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;
    • (1989) Biochem , vol.28 , pp. 1763-1769
    • Reddy, G.S.1    Tserng, K.Y.2
  • 5
    • 84884872452 scopus 로고    scopus 로고
    • Vitamin D metabolism
    • 2nd ed, D. Feldman, F. H. Glorieux, and J. W. Pike Eds, Academic Press: Amsterdam
    • (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.
    • (2005) Vitamin D , vol.1 , pp. 15-35
    • Horst, R.L.1    Reinhardt, T.A.2    Reddy, G.S.3
  • 6
    • 0000344537 scopus 로고
    • A synthetic method for formyl→ethynyl conversion (RCHO→RC≡CH or RC≡CR′)
    • 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.
    • (1972) Tetrahedron Lett , vol.13 , pp. 3769-3772
    • Corey, E.J.1    Fuchs, P.L.2
  • 7
    • 33947473632 scopus 로고
    • A new synthesis of 1,1-dibromoölefins via phosphine-dibromomethylenes: The reaction of triphenylphosphine with carbon tetrabromide
    • 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.
    • (1962) J. Amer. Chem. Soc , vol.84 , pp. 1745-1747
    • Ramirez, F.1    Desai, N.B.2    McKelvie, N.3
  • 8
    • 0036456217 scopus 로고    scopus 로고
    • Safety-catch propargyl-based linker strategy for the immobilization of amines and carboxylic acids in SPOS
    • 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.
    • (2002) Synlett , vol.12 , pp. 1991-1994
    • Fürst, M.1    Rück-Braun, K.2
  • 9
    • 84936299305 scopus 로고
    • Reactions with phosphinealkylenes, 39: New methods for the preparation of 1-bromoacetylenes and aromatic and conjugated enynes
    • 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.
    • (1980) Liebigs Ann. Chem , pp. 2061-2071
    • Bestmann, H.J.1    Frey, H.2
  • 12
    • 0001614693 scopus 로고
    • Stereoselective methods for the synthesis of terminal cis and trans enyne units
    • (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;
    • (1973) Tetrahedron Lett , vol.14 , pp. 1495-1499
    • Corey, E.J.1    Ruden, R.A.2
  • 13
    • 84987505467 scopus 로고
    • Synthesis, isolation, and NMR-spectroscopic characterization of fourteen (Z)-isomers of lycopene and of some acetylenic didehydro- and tetradehydrolycopenes
    • (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;
    • (1992) Helv. Chim. Acta , vol.75 , pp. 1848-1865
    • Hengartner, U.1    Bernhard, K.2    Meyer, K.3    Englert, G.4    Glinz, E.5
  • 14
    • 0029990258 scopus 로고    scopus 로고
    • A new stereocontrolled, pyrylium-based route to conjugated dienynes: The first synthesis of carduusyne A
    • (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.
    • (1996) Tetrahedron Lett , vol.37 , pp. 1913-1916
    • Charoenying, P.1    Davies, D.H.2    McKerrecher, D.3    Taylor, R.J.K.4
  • 15
    • 0033521149 scopus 로고    scopus 로고
    • A one-pot procedure for the synthesis of alkynes and bromoalkynes from aldehydes
    • 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.
    • (1996) Tetrahedron Lett , vol.40 , pp. 8575-8578
    • Michel, P.1    Gennet, D.2    Rassat, A.3
  • 16
    • 0030459326 scopus 로고    scopus 로고
    • An improved synthesis of dichloroalkylphosphonates, chloroalkynes, and terminal alkynes via diethyl dichloromethylphosphonate
    • 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.
    • (1996) Synthesis , vol.12 , pp. 1494-1498
    • Carran, J.1    Waschbüsch, R.2    Marinetti, A.3    Savignac, P.4
  • 17
    • 37049109989 scopus 로고
    • A simple procedure for the elaboration of carbonyl compounds into homologous alkynes
    • (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;
    • (1977) J. Chem. Soc. Perkin Trans. 1 , pp. 869-874
    • Colvin, E.W.1    Hamill, B.J.2
  • 18
    • 37049117445 scopus 로고
    • One-step conversion of carbonyl compounds into acetylenes
    • (b) Colvin, E. W.; Hamill, B. J. One-step conversion of carbonyl compounds into acetylenes. J. Chem. Soc., Chem. Commun. 1973, 151-152.
    • (1973) J. Chem. Soc., Chem. Commun , pp. 151-152
    • Colvin, E.W.1    Hamill, B.J.2
  • 19
    • 33745728273 scopus 로고    scopus 로고
    • Reaction of C-silylated α-diazophosphines as nucleophiles toward carbonyl compounds: A mechanistic study and application to the synthesis of alkynes and α-hydroxyphosphonamides
    • 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.
    • (2006) J. Org. Chem , vol.71 , pp. 5320-5327
    • Illa, O.1    Bagan, X.2    Cazorla, A.M.3    Lyon, C.4    Baceiredo, A.5    Branchadell, V.6    Ortuno, R.M.7
  • 20
    • 0002957219 scopus 로고
    • Extension of the Colvin rearrangement using trimethylsilyldiazomethane: A new synthesis of alkynes
    • (a) Miwa, K.; Shioiri, T.; Aoyama, T. Extension of the Colvin rearrangement using trimethylsilyldiazomethane: A new synthesis of alkynes. Synlett 1994, 107-108;
    • (1994) Synlett , pp. 107-108
    • Miwa, K.1    Shioiri, T.2    Aoyama, T.3
  • 21
    • 0003160578 scopus 로고    scopus 로고
    • A new preparation of benzofurans utilizing trimethylsilyldiazomethane
    • (b) Ito, Y.; Aoyama, T.; Shioiri, T. A new preparation of benzofurans utilizing trimethylsilyldiazomethane. Synlett 1997, 10, 1163-1164.
    • (1997) Synlett , vol.10 , pp. 1163-1164
    • Ito, Y.1    Aoyama, T.2    Shioiri, T.3
  • 22
    • 84985677205 scopus 로고
    • Diazo compounds and azides, XIII: Mercuric and silver derivatives from diphenylphosphinyl-and diethylphosphonodiazomethane
    • 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.
    • (1971) Liebigs Ann. Chem , vol.748 , pp. 207-210
    • Regitz, M.1    Liedhegener, A.2    Eckstein, U.3    Martin, M.4    Anschuetz, W.5
  • 24
    • 0001517035 scopus 로고    scopus 로고
    • A convenient synthesis of dimethyl (diazomethyl)phosphonate (Seyferth/Gilbert reagent)
    • 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.
    • (1996) J. Org. Chem , vol.61 , pp. 2540-2541
    • Brown, D.G.1    Velthuisen, E.J.2    Commerford, J.R.3    Brisbois, R.G.4    Hoye, T.R.5
  • 25
    • 0001174986 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 26
    • 1542504084 scopus 로고    scopus 로고
    • An improved one-pot procedure for the synthesis of alkynes from aldehydes
    • 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.
    • (1996) Synlett , pp. 521-522
    • Müller, S.1    Liepold, B.2    Roth, G.J.3    Bestmann, H.J.4
  • 27
    • 0037124480 scopus 로고    scopus 로고
    • Practical one-step synthesis of ethynylglycine synthon from Garner's aldehyde
    • 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.
    • (2002) Tetrahedron , vol.58 , pp. 5159-5162
    • Meffre, P.1    Hermann, S.2    Durand, P.3    Reginato, G.4    Riu, A.5
  • 28
    • 0346688599 scopus 로고    scopus 로고
    • Further improvements of the synthesis of alkynes from aldehydes
    • Roth, G. J.; Liepold, B.; Müller, S. G.; Bestmann, H. J. Further improvements of the synthesis of alkynes from aldehydes. Synthesis 2004, 59-61.
    • (2004) Synthesis , pp. 59-61
    • Roth, G.J.1    Liepold, B.2    Müller, S.G.3    Bestmann, H.J.4
  • 29
    • 84949695566 scopus 로고
    • Methanolysis of dimethyl (1-diazo-2-oxopropyl)phosphonate: Generation of dimethyl (diazomethyl)phosphonate and reaction with carbonyl compounds
    • 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.
    • (1989) Synth. Commun , vol.19 , pp. 561-564
    • Ohira, S.1
  • 30
    • 1642409290 scopus 로고    scopus 로고
    • Parallel synthesis of terminal alkynes using a ROMPgel-supported ethyl 1-diazo-2-oxopropylphosphonate
    • (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;
    • (2004) Org. Lett , vol.6 , pp. 835-837
    • Barrett, A.G.M.1    Hopkins, B.T.2    Love, A.C.3    Tedeschi, L.4
  • 32
    • 33845375462 scopus 로고
    • Mesyl azide: A superior reagent for diazo transfer
    • 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.
    • (1986) J. Org. Chem , vol.51 , pp. 4077-4078
    • Taber, D.F.1    Ruckle Jr., R.E.2    Hennessy, M.J.3
  • 33
    • 0028947643 scopus 로고
    • An improved and efficient method for diazo transfer reaction of active methylene compounds
    • 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.
    • (1995) Synth. Commun , vol.25 , pp. 1511-1515
    • Lee, J.C.1    Yuk, J.Y.2
  • 34
    • 0000439292 scopus 로고
    • A selective and efficient method for alcohol oxidations mediated by N-oxoammonium salts in combination with sodium bromite
    • (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;
    • (1990) J. Org. Chem , vol.55 , pp. 462-466
    • Inokuchi, T.1    Matsumoto, S.2    Nishiyama, T.3    Torii, S.4
  • 35
    • 0025219293 scopus 로고
    • Selective oxidation of primary hydroxy groups in prinary-secondary diols
    • (b) Siedlecka, R.; Skarzewski, J.; Mlochowski, J. Selective oxidation of primary hydroxy groups in prinary-secondary diols. Tetrahedron Lett. 1990, 31, 2177-2180;
    • (1990) Tetrahedron Lett , vol.31 , pp. 2177-2180
    • Siedlecka, R.1    Skarzewski, J.2    Mlochowski, J.3
  • 36
    • 0001097669 scopus 로고    scopus 로고
    • Efficient and highly selective oxidation of primary alcohols to aldehydes by N-chlorosuccinimide mediated by oxoammonium salts
    • (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.
    • (1996) J. Org. Chem , vol.61 , pp. 7452-7454
    • Einhorn, J.1    Einhorn, C.2    Ratajczak, F.3    Pierre, J.-L.4
  • 37
    • 0029977310 scopus 로고    scopus 로고
    • On a safe and practical method fort he preparation of β-keto phosphonates
    • 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.
    • (1996) Synth. Commun , vol.26 , pp. 2561-2568
    • Corbel, B.1    L'Hostis-Kervella, I.2    Haelters, J.-P.3
  • 38
    • 14844291472 scopus 로고    scopus 로고
    • Design, synthesis, and evaluation of 2,4-diaminoquinazolines as inhibitors of trypanosomal and leishmanial dihydrofolate reductase
    • 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.
    • (2005) Bioorg. Med. Chem , vol.13 , pp. 2637-2649
    • Khabnadideh, S.1    Didier Pez, D.2    Musso, A.3    Brun, R.4    Ruiz Pérez, L.M.5    González-Pacanowska, D.6    Gilbert, I.H.7
  • 39
    • 37049100221 scopus 로고
    • Calciferol and its relatives, part 20: A synthesis of Windaus and Grundmann's C19 ketone
    • 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.
    • (1977) J. Chem. Soc. Perkin Trans. 1 , pp. 2608-2612
    • Lythgoe, B.1    Roberts, D.A.2    Waterhouse, I.3
  • 40
  • 41
    • 58149111413 scopus 로고    scopus 로고
    • Preparation of arylsecocholadiene derivatives with vitamin D activity
    • WO Patent, 9847866
    • Barbier, P.; Bauer, F.; Mohr, P.; Muller, M.; Pirson, W. Preparation of arylsecocholadiene derivatives with vitamin D activity. WO Patent, 9847866, 1998.
    • (1998)
    • Barbier, P.1    Bauer, F.2    Mohr, P.3    Muller, M.4    Pirson, W.5
  • 42
    • 58149106448 scopus 로고    scopus 로고
    • 3 analogs for pharmaceutical use. WO Patent, 9912894, 1999
    • 3 analogs for pharmaceutical use. WO Patent, 9912894, 1999.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.