메뉴 건너뛰기




Volumn 64, Issue 22, 1999, Pages 8406-8408

Convenient preparations of (diphenylphosphono)acetic acid esters and the comparison of the Z-selectivities of their Horner-Wadsworth-Emmons reaction with aldehydes depending on the ester moiety

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BIPHENYL DERIVATIVE; BROMOACETIC ACID; METHYLPHOSPHONIC ACID; PHOSPHITE; PHOSPHONIC ACID ESTER; PHOSPHONOACETIC ACID; TETRAHYDROFURAN; TRIMETHYLAMMONIUM SALT DERIVATIVE;

EID: 0033615594     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9907181     Document Type: Article
Times cited : (114)

References (34)
  • 1
    • 0001848341 scopus 로고
    • Reviews of Horner - Wadsworth - Emmons reaction: Maryanoff, B. E.; Reitz, A. B.; Chem. Rev. 1989, 89, 863-927; Boutagy, J.; Thomas, R. Chem. Rev. 1974, 74, 87-99. For asymmetric versions of the HWE reaction, see: Rein, T.; Reiser, O. Acta Chem. Scand. 1998, 50, 369-379.
    • (1989) Chem. Rev. , vol.89 , pp. 863-927
    • Maryanoff, B.E.1    Reitz, A.B.2
  • 2
    • 33847803678 scopus 로고
    • Reviews of Horner - Wadsworth - Emmons reaction: Maryanoff, B. E.; Reitz, A. B.; Chem. Rev. 1989, 89, 863-927; Boutagy, J.; Thomas, R. Chem. Rev. 1974, 74, 87-99. For asymmetric versions of the HWE reaction, see: Rein, T.; Reiser, O. Acta Chem. Scand. 1998, 50, 369-379.
    • (1974) Chem. Rev. , vol.74 , pp. 87-99
    • Boutagy, J.1    Thomas, R.2
  • 3
    • 3242866355 scopus 로고    scopus 로고
    • Reviews of Horner - Wadsworth - Emmons reaction: Maryanoff, B. E.; Reitz, A. B.; Chem. Rev. 1989, 89, 863-927; Boutagy, J.; Thomas, R. Chem. Rev. 1974, 74, 87-99. For asymmetric versions of the HWE reaction, see: Rein, T.; Reiser, O. Acta Chem. Scand. 1998, 50, 369-379.
    • (1998) Acta Chem. Scand. , vol.50 , pp. 369-379
    • Rein, T.1    Reiser, O.2
  • 4
    • 0032887595 scopus 로고    scopus 로고
    • For mechanistic studies of HWE reaction: Ando, K. J. Org. Chem. 1999, 64, 6815-6821 and references therein.
    • (1999) Org. Chem. , vol.64 , pp. 6815-6821
    • Ando, K.J.1
  • 10
    • 0000262852 scopus 로고    scopus 로고
    • (b) Ando, K. J. Org. Chem. 1997, 62, 1934-1939.
    • (1997) J. Org. Chem. , vol.62 , pp. 1934-1939
    • Ando, K.1
  • 11
  • 13
    • 0030054270 scopus 로고    scopus 로고
    • Abiko, A.; Masamune, S. Tetrahedron Lett. 1996, 37, 1077-1080. Kreuder, R.; Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035-9038. Zhang, T. Y.; O'Toole J. C.; Dunigan, J. M. Tetrahedron Lett. 1998, 39, 1461-1464.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 1077-1080
    • Abiko, A.1    Masamune, S.2
  • 14
    • 0030830481 scopus 로고    scopus 로고
    • Abiko, A.; Masamune, S. Tetrahedron Lett. 1996, 37, 1077-1080. Kreuder, R.; Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035-9038. Zhang, T. Y.; O'Toole J. C.; Dunigan, J. M. Tetrahedron Lett. 1998, 39, 1461-1464.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 9035-9038
    • Kreuder, R.1    Rein, T.2    Reiser, O.3
  • 15
    • 0032546214 scopus 로고    scopus 로고
    • Abiko, A.; Masamune, S. Tetrahedron Lett. 1996, 37, 1077-1080. Kreuder, R.; Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035-9038. Zhang, T. Y.; O'Toole J. C.; Dunigan, J. M. Tetrahedron Lett. 1998, 39, 1461-1464.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 1461-1464
    • Zhang, T.Y.1    O'Toole J, C.2    Dunigan, J.M.3
  • 19
    • 0000568967 scopus 로고
    • Mikolajczyk, M.; Mikina, M. J. Org. Chem. 1994, 59, 6760-6765. Geirsson, J. K. F.; Njardarson, J. T. Tetrahedron Lett. 1994, 35, 9071-9072. Gil, J. M.; Hah, J. H.; Park, K. Y.; Oh, D. Y. Tetrahedron Lett. 1998, 39, 3205-3208.
    • (1994) J. Org. Chem. , vol.59 , pp. 6760-6765
    • Mikolajczyk, M.1    Mikina, M.2
  • 20
    • 0028079794 scopus 로고
    • Mikolajczyk, M.; Mikina, M. J. Org. Chem. 1994, 59, 6760-6765. Geirsson, J. K. F.; Njardarson, J. T. Tetrahedron Lett. 1994, 35, 9071-9072. Gil, J. M.; Hah, J. H.; Park, K. Y.; Oh, D. Y. Tetrahedron Lett. 1998, 39, 3205-3208.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 9071-9072
    • Geirsson, J.K.F.1    Njardarson, J.T.2
  • 21
    • 0032516326 scopus 로고    scopus 로고
    • Mikolajczyk, M.; Mikina, M. J. Org. Chem. 1994, 59, 6760-6765. Geirsson, J. K. F.; Njardarson, J. T. Tetrahedron Lett. 1994, 35, 9071-9072. Gil, J. M.; Hah, J. H.; Park, K. Y.; Oh, D. Y. Tetrahedron Lett. 1998, 39, 3205-3208.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 3205-3208
    • Gil, J.M.1    Hah, J.H.2    Park, K.Y.3    Oh, D.Y.4
  • 22
    • 0026325277 scopus 로고
    • The anion derived from bis(trifluoroethyl) alkylphosphonate is also not stable even at low temperature: Patois, C.; Savignac, P. Synth. Commun. 1991, 21, 2391-2396.
    • (1991) Synth. Commun. , vol.21 , pp. 2391-2396
    • Patois, C.1    Savignac, P.2
  • 23
    • 33947438112 scopus 로고
    • Kosolapoff, G. M. J. Am. Chem. Soc. 1945, 67, 1180-1182. Myers, T. C.; Preis, S.; Jensen, E. V. J. Am. Chem. Soc. 1954, 76, 4172-4173.
    • (1945) J. Am. Chem. Soc. , vol.67 , pp. 1180-1182
    • Kosolapoff, G.M.1
  • 26
    • 0032497716 scopus 로고    scopus 로고
    • Base-and/or acid-catalyzed addition of dialkyl phosphites to aldehydes is a recent topic: Simoni, D.; Invidiata, F. P.; Manferdini, M.; Lampronti, I.; Rondanin, R.; Boberti, M.; Pollini, G. P. Tetrahedron Lett. 1998, 39, 7615-7618. Groaning, M. D.; Rowe, B. J.; Spilling, C. D. Tetrahedron Lett. 1998, 39, 5485-5488. Yokomatsu, T.; Yamagishi, T.; Shibuya, S. J. Chem. Soc., Perkin Trans. 1 1997, 1527-1533. Arai, T.; Bougauchi, M. Sasai, H.; Shibasaki, M. J. Org. Chem. 1996, 61, 2926-2927.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 7615-7618
    • Simoni, D.1    Invidiata, F.P.2    Manferdini, M.3    Lampronti, I.4    Rondanin, R.5    Boberti, M.6    Pollini, G.P.7
  • 27
    • 0032581679 scopus 로고    scopus 로고
    • Base-and/or acid-catalyzed addition of dialkyl phosphites to aldehydes is a recent topic: Simoni, D.; Invidiata, F. P.; Manferdini, M.; Lampronti, I.; Rondanin, R.; Boberti, M.; Pollini, G. P. Tetrahedron Lett. 1998, 39, 7615-7618. Groaning, M. D.; Rowe, B. J.; Spilling, C. D. Tetrahedron Lett. 1998, 39, 5485-5488. Yokomatsu, T.; Yamagishi, T.; Shibuya, S. J. Chem. Soc., Perkin Trans. 1 1997, 1527-1533. Arai, T.; Bougauchi, M. Sasai, H.; Shibasaki, M. J. Org. Chem. 1996, 61, 2926-2927.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 5485-5488
    • Groaning, M.D.1    Rowe, B.J.2    Spilling, C.D.3
  • 28
    • 33748734506 scopus 로고    scopus 로고
    • Base-and/or acid-catalyzed addition of dialkyl phosphites to aldehydes is a recent topic: Simoni, D.; Invidiata, F. P.; Manferdini, M.; Lampronti, I.; Rondanin, R.; Boberti, M.; Pollini, G. P. Tetrahedron Lett. 1998, 39, 7615-7618. Groaning, M. D.; Rowe, B. J.; Spilling, C. D. Tetrahedron Lett. 1998, 39, 5485-5488. Yokomatsu, T.; Yamagishi, T.; Shibuya, S. J. Chem. Soc., Perkin Trans. 1 1997, 1527-1533. Arai, T.; Bougauchi, M. Sasai, H.; Shibasaki, M. J. Org. Chem. 1996, 61, 2926-2927.
    • (1997) J. Chem. Soc., Perkin Trans. 1 , pp. 1527-1533
    • Yokomatsu, T.1    Yamagishi, T.2    Shibuya, S.3
  • 29
    • 0029981019 scopus 로고    scopus 로고
    • Base-and/or acid-catalyzed addition of dialkyl phosphites to aldehydes is a recent topic: Simoni, D.; Invidiata, F. P.; Manferdini, M.; Lampronti, I.; Rondanin, R.; Boberti, M.; Pollini, G. P. Tetrahedron Lett. 1998, 39, 7615-7618. Groaning, M. D.; Rowe, B. J.; Spilling, C. D. Tetrahedron Lett. 1998, 39, 5485-5488. Yokomatsu, T.; Yamagishi, T.; Shibuya, S. J. Chem. Soc., Perkin Trans. 1 1997, 1527-1533. Arai, T.; Bougauchi, M. Sasai, H.; Shibasaki, M. J. Org. Chem. 1996, 61, 2926-2927.
    • (1996) J. Org. Chem. , vol.61 , pp. 2926-2927
    • Arai, T.1    Bougauchi, M.2    Sasai, H.3    Shibasaki, M.4
  • 30
    • 84953461121 scopus 로고    scopus 로고
    • note
    • There is a byproduct which cannot be removed by distillation from 3a. This byproduct gradually decomposes to PhOH and nonvolatile compounds, which can be removed by distillation. Although acid (2 mol/L HCl) or base (2 mol/L NaOH) treatment of the crude mixture did not promote the decomposition of this byproduct, keeping the crude mixture in the air for a few days and bulb-to-bulb distillation (250 °C/3 mmHg) gave ∼95% pure 3a. (15) The reactions of ethyl and methyl bis(trifluoroethyl)phosphonoacetate with aminoaldehyde were reported. Hensel, M. J.; Fuchs, P. L. Synth. Commun. 1986, 16, 1285-1295.
  • 31
    • 0344300723 scopus 로고    scopus 로고
    • note
    • For the error margin, it would be safe to think the ratio 86:14 (6.1:1) as 84-88% Z, the ratio 90:10 (9:1) as 89-91% Z, and the ratio 95:5 (19:1) as 94.3-95.7% Z.
  • 33
    • 0015948923 scopus 로고
    • For the preparation of α,β-unaaturated acids by HWE reaction, see: Koppel, G. A.; Kinnick, M. D. Tetrahedron Lett. 1974, 711-713. Combardo, L.; Taylor, R. J. K. Synthesis 1978, 131-132.
    • (1974) Tetrahedron Lett. , pp. 711-713
    • Koppel, G.A.1    Kinnick, M.D.2
  • 34
    • 0011528389 scopus 로고
    • For the preparation of α,β-unaaturated acids by HWE reaction, see: Koppel, G. A.; Kinnick, M. D. Tetrahedron Lett. 1974, 711-713. Combardo, L.; Taylor, R. J. K. Synthesis 1978, 131-132.
    • (1978) Synthesis , pp. 131-132
    • Combardo, L.1    Taylor, R.J.K.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.