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Volumn 130, Issue 25, 2008, Pages 7955-7966

Asymmetric aza-Henry reaction under phase transfer catalysis: An experimental and theoretical study

Author keywords

[No Author keywords available]

Indexed keywords

REACTION KINETICS; SULFUR COMPOUNDS;

EID: 45749157617     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja800253z     Document Type: Article
Times cited : (144)

References (104)
  • 3
    • 0037434136 scopus 로고    scopus 로고
    • For a highlight disclosing recent catalytic asymmetric approaches, see: c
    • For a highlight disclosing recent catalytic asymmetric approaches, see: (c) Westermann, B Angew. Chem., Int. Ed. 2003, 42, 151-153.
    • (2003) Angew. Chem., Int. Ed , vol.42 , pp. 151-153
    • Westermann, B.1
  • 4
    • 0001165505 scopus 로고
    • Reviews on the Nef reaction: (a) Pinnick, H. W
    • Reviews on the Nef reaction: (a) Pinnick, H. W. Org. Reac. 1990, 38, 655-792.
    • (1990) Org. Reac , vol.38 , pp. 655-792
  • 6
    • 35448961213 scopus 로고    scopus 로고
    • For the synthesis of fine chemicals from nitroalkanes, see: c
    • For the synthesis of fine chemicals from nitroalkanes, see: (c) Ballini, R.; Palmieri, A.; Right, P. Tetrahedron 2007, 63, 12099-12121.
    • (2007) Tetrahedron , vol.63 , pp. 12099-12121
    • Ballini, R.1    Palmieri, A.2    Right, P.3
  • 18
    • 1342268984 scopus 로고    scopus 로고
    • Bifunctional thioureas: (b) Okino, T.; Nakamura, S.; Furukawa, T.; Takemoto, Y. Org. Lett. 2004, 6, 625-627.
    • Bifunctional thioureas: (b) Okino, T.; Nakamura, S.; Furukawa, T.; Takemoto, Y. Org. Lett. 2004, 6, 625-627.
  • 22
    • 37049000818 scopus 로고    scopus 로고
    • N-Sulfinyl ureas: (f) Robak, M. T.; Trincado, M.; Ellman, J. A. J. Am. Chem. Soc. 2007, 129, 15110-15111.
    • N-Sulfinyl ureas: (f) Robak, M. T.; Trincado, M.; Ellman, J. A. J. Am. Chem. Soc. 2007, 129, 15110-15111.
  • 23
    • 45749157179 scopus 로고    scopus 로고
    • For some examples of addition of long chain or functionalized nitroalkanes, see refs 5, 6b, d, 7b, 8c, d, and 8f
    • For some examples of addition of long chain or functionalized nitroalkanes, see refs 5, 6b, d, 7b, 8c, d, and 8f.
  • 25
    • 45749150733 scopus 로고    scopus 로고
    • For recent examples of enantioselective aza-Henry reaction with aliphatic N-Boc imines, see refs 6d and 8f.
    • For recent examples of enantioselective aza-Henry reaction with aliphatic N-Boc imines, see refs 6d and 8f.
  • 30
    • 28444495479 scopus 로고    scopus 로고
    • For a review on the preparation and reactivity of α-amidosulfones, see: a
    • For a review on the preparation and reactivity of α-amidosulfones, see: (a) Petrini, M. Chem. Rev 2005, 105, 3949-3977.
    • (2005) Chem. Rev , vol.105 , pp. 3949-3977
    • Petrini, M.1
  • 34
    • 33847782578 scopus 로고    scopus 로고
    • W; Deng, L
    • (e) Song, J.; Shih, H.; W; Deng, L Org. Lett. 2007, 9, 603-606.
    • (2007) Org. Lett , vol.9 , pp. 603-606
    • Song, J.1    Shih, H.2
  • 36
    • 0042880949 scopus 로고    scopus 로고
    • For cinchone-based quaternary ammonium salts catalyzed reactions, see: a
    • For cinchone-based quaternary ammonium salts catalyzed reactions, see: (a) Maruoka, K.; Oii, T. Chem. Rev. 2003, 103, 3013-3028.
    • (2003) Chem. Rev , vol.103 , pp. 3013-3028
    • Maruoka, K.1    Oii, T.2
  • 40
    • 38349148300 scopus 로고    scopus 로고
    • For a recent review on the application of phase transfer catalysts, see: e
    • For a recent review on the application of phase transfer catalysts, see: (e) Hashimoto, T.; Maruoka, K. Chem. Rev. 2007, 107, 5656-5682.
    • (2007) Chem. Rev , vol.107 , pp. 5656-5682
    • Hashimoto, T.1    Maruoka, K.2
  • 41
    • 45749130581 scopus 로고    scopus 로고
    • The corresponding N-phosphinoyl protected α-amido sulfone did not react under the PTC conditions employed. The enantiomeric purities were determined by HPLC.
    • The corresponding N-phosphinoyl protected α-amido sulfone did not react under the PTC conditions employed. The enantiomeric purities were determined by HPLC.
  • 42
    • 45749133852 scopus 로고    scopus 로고
    • In control experiments, the d.r. values of the reaction of 1a and 1b were measured at different degrees of reaction conversion, observing no dependence of the d.r. value with conversion.
    • In control experiments, the d.r. values of the reaction of 1a and 1b were measured at different degrees of reaction conversion, observing no dependence of the d.r. value with conversion.
  • 43
    • 45749104059 scopus 로고    scopus 로고
    • See refs 7a and 8c
    • See refs 7a and 8c.
  • 44
    • 0031189711 scopus 로고    scopus 로고
    • For references on the topic, see: a
    • For references on the topic, see: (a) Babine, R. E.; Bender, S. L. Chem. Rev. 1997, 97, 1359-1472.
    • (1997) Chem. Rev , vol.97 , pp. 1359-1472
    • Babine, R.E.1    Bender, S.L.2
  • 47
    • 45749106342 scopus 로고    scopus 로고
    • Due to some discrepancy in the absolute value of the optical rotation, relative configuration was confirmed by X-ray crystal structural analysis of adduct 6x.
    • Due to some discrepancy in the absolute value of the optical rotation, relative configuration was confirmed by X-ray crystal structural analysis of adduct 6x.
  • 48
    • 0030761511 scopus 로고    scopus 로고
    • For adduct 12, see: (a) Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1997, 8, 2381-2401.
    • For adduct 12, see: (a) Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1997, 8, 2381-2401.
  • 49
    • 0022869306 scopus 로고    scopus 로고
    • For adduct 13, see: (b) Arrowsmith, R.; Carter, K.; Dann, J. G.; Davies, D. E.; Harris, J.; Morton, J. A.; Lister, P.; Robinson, J. A.; Williams, D. J. Chem. Soc., Chem. Commun. 1986, 755-757.
    • For adduct 13, see: (b) Arrowsmith, R.; Carter, K.; Dann, J. G.; Davies, D. E.; Harris, J.; Morton, J. A.; Lister, P.; Robinson, J. A.; Williams, D. J. Chem. Soc., Chem. Commun. 1986, 755-757.
  • 51
    • 45749094152 scopus 로고    scopus 로고
    • Transformation of 14x into the corresponding knownγ- aminoα,β-unsaturated acid 15 allowed the determination of the absolute configuration (see Supporting Information). The enantiomeric purity was determined by HPLC.
    • Transformation of 14x into the corresponding knownγ- aminoα,β-unsaturated acid 15 allowed the determination of the absolute configuration (see Supporting Information). The enantiomeric purity was determined by HPLC.
  • 52
    • 0038650519 scopus 로고    scopus 로고
    • Access to these interesting compounds has traditionally relied on the olefination of α-amino aldehydes. See, for instance: (a) Gryko, D, Chalko, J, Jurczak, J. Chirality 2003, 15, 514-541
    • Access to these interesting compounds has traditionally relied on the olefination of α-amino aldehydes. See, for instance: (a) Gryko, D.; Chalko, J.; Jurczak, J. Chirality 2003, 15, 514-541.
  • 53
    • 0000763561 scopus 로고    scopus 로고
    • (b) Reetz, M. T Chem. Rev. 1999, 99, 1121-1162.
    • (1999) Chem. Rev , vol.99 , pp. 1121-1162
    • Reetz, M.T.1
  • 62
    • 0037069729 scopus 로고    scopus 로고
    • Peptide isosters: (a) Thoen, J. C.; Morales-Ramos, A. I.; Lipton, M. A. Org. Lett. 2002, 4, 4455-4458.
    • Peptide isosters: (a) Thoen, J. C.; Morales-Ramos, A. I.; Lipton, M. A. Org. Lett. 2002, 4, 4455-4458.
  • 65
    • 0141852863 scopus 로고    scopus 로고
    • Iminosugars: (d) Hulme, A. N.; Montgomery, C. H Tetrahedron Lett. 2003, 44, 7649-7653.
    • Iminosugars: (d) Hulme, A. N.; Montgomery, C. H Tetrahedron Lett. 2003, 44, 7649-7653.
  • 66
    • 0037064592 scopus 로고    scopus 로고
    • Glutamate receptors: (e) Oba, M.; Koguchi, S.; Nishiyama, K. Tetrahedron 2002, 58, 9359-9363.
    • Glutamate receptors: (e) Oba, M.; Koguchi, S.; Nishiyama, K. Tetrahedron 2002, 58, 9359-9363.
  • 69
    • 33845183545 scopus 로고    scopus 로고
    • Amino acids: (h) Hayashi, T.; Yamamoto, A.; Ito, Y.; Nishioka, E.; Miura, H.; Yanagi, K. J. Am. Chem. Soc. 1989, 111, 6301-6311.
    • Amino acids: (h) Hayashi, T.; Yamamoto, A.; Ito, Y.; Nishioka, E.; Miura, H.; Yanagi, K. J. Am. Chem. Soc. 1989, 111, 6301-6311.
  • 75
    • 0347584753 scopus 로고    scopus 로고
    • Carbohydrate derivatives: (n) Trost, B. M.; Van Vranken, D. L. J. Am. Chem. Soc. 1993, 115, 444-458.
    • Carbohydrate derivatives: (n) Trost, B. M.; Van Vranken, D. L. J. Am. Chem. Soc. 1993, 115, 444-458.
  • 76
    • 84981810671 scopus 로고
    • For reviews on the topic, see: a
    • For reviews on the topic, see: (a) Seebach, D. Angew. Chem., Int. Ed. Engl. 1969, 8, 639-649.
    • (1969) Angew. Chem., Int. Ed. Engl , vol.8 , pp. 639-649
    • Seebach, D.1
  • 77
    • 45749104058 scopus 로고    scopus 로고
    • Umpoled Synthons; Hase, T. A., Ed.; John Wiley: New York, 1987.
    • (b) Umpoled Synthons; Hase, T. A., Ed.; John Wiley: New York, 1987.
  • 78
    • 37049137712 scopus 로고    scopus 로고
    • To the best of our knowledge, base-promoted elimination of nitrous acid to afford alkenes has only been employed in combination with racemic transformations: Michael addition to ethyl β-nitroacrylate: (a) Patterson, J. W.; McMurry, J. E. Chem. Commun. 1971, 488-489.
    • To the best of our knowledge, base-promoted elimination of nitrous acid to afford alkenes has only been employed in combination with racemic transformations: Michael addition to ethyl β-nitroacrylate: (a) Patterson, J. W.; McMurry, J. E. Chem. Commun. 1971, 488-489.
  • 79
    • 84980187463 scopus 로고    scopus 로고
    • Henry and Michael reactions of nitroalkanes: (b) Seebach, D.; Hoekstra, M. S.; Protschuck, G. Angew. Chem., Int. Ed. 1977, 16, 321-322.
    • Henry and Michael reactions of nitroalkanes: (b) Seebach, D.; Hoekstra, M. S.; Protschuck, G. Angew. Chem., Int. Ed. 1977, 16, 321-322.
  • 84
    • 0000536382 scopus 로고    scopus 로고
    • Alkylation of nitroesters: (g) Seebach, D.; Henning, R.; Mukhopadhyay, T Chem. Ber. 1982, 115, 1705-1720.
    • Alkylation of nitroesters: (g) Seebach, D.; Henning, R.; Mukhopadhyay, T Chem. Ber. 1982, 115, 1705-1720.
  • 85
    • 0000593953 scopus 로고    scopus 로고
    • Diels-Alder reactions: (h) Danishesfsky, S.; Prisbylla, M. P.; Hiner, S. J. Am. Chem. Soc. 1978, 100, 2918-2920.
    • Diels-Alder reactions: (h) Danishesfsky, S.; Prisbylla, M. P.; Hiner, S. J. Am. Chem. Soc. 1978, 100, 2918-2920.
  • 86
    • 33845943259 scopus 로고    scopus 로고
    • For related proposals involving catalytic PTC reaction conditions, see: Mannich reaction: ref 15b; Strecker reaction: Herrera, R. P.; Sgarnazi, V.; Bernadi, L.; Fini, F.; Pettersen, D.; Ricci, A. J. Org. Chem. 2006, 71, 9869-9872.
    • For related proposals involving catalytic PTC reaction conditions, see: Mannich reaction: ref 15b; Strecker reaction: Herrera, R. P.; Sgarnazi, V.; Bernadi, L.; Fini, F.; Pettersen, D.; Ricci, A. J. Org. Chem. 2006, 71, 9869-9872.
  • 87
    • 33746323982 scopus 로고    scopus 로고
    • Substrate solubility constraints were found during kinetic studies of a thiourea-catalyzed Michael reaction to unsaturated imides. See: (a) Inokuma, T, Hoashi, Y, Takemoto, Y. J. Am. Chem. Soc. 2006, 128, 9413-9419
    • Substrate solubility constraints were found during kinetic studies of a thiourea-catalyzed Michael reaction to unsaturated imides. See: (a) Inokuma, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2006, 128, 9413-9419.
  • 91
    • 45749151724 scopus 로고    scopus 로고
    • Frisch, M. J.; Gaussian 03, revision D.03; Gaussian, Inc.: Wallingford, CT, 2004.
    • Frisch, M. J.; Gaussian 03, revision D.03; Gaussian, Inc.: Wallingford, CT, 2004.
  • 98
    • 0037134937 scopus 로고    scopus 로고
    • +-CH⋯O=C hydrogen bonds have been reported to be the strongest hydrogen bonds of the type C-H⋯O=C known to date: Cannizaro, C. E.; Houk, K. N. J. Am. Chem. Soc. 2002, 124, 7163-7169.
    • +-CH⋯O=C hydrogen bonds have been reported to be the strongest hydrogen bonds of the type C-H⋯O=C known to date: Cannizaro, C. E.; Houk, K. N. J. Am. Chem. Soc. 2002, 124, 7163-7169.
  • 99
    • 84962467066 scopus 로고    scopus 로고
    • For previous theoretical studies dealing with organocatalytic reactions where the catalyst exhibits two competitive H-bond donor sites, see: (a) Hamza, A, Schubert, G, Soós, T, Papai, I. J. Am. Chem. Soc. 2006, 128, 13151-13160
    • For previous theoretical studies dealing with organocatalytic reactions where the catalyst exhibits two competitive H-bond donor sites, see: (a) Hamza, A.; Schubert, G.; Soós, T.; Papai, I. J. Am. Chem. Soc. 2006, 128, 13151-13160.
  • 101
    • 45749100064 scopus 로고    scopus 로고
    • This findings are in agreement with the reported data about the strength of hydrogen bonds of the type Me3N+-CH⋯O=C, see ref 39
    • +-CH⋯O=C, see ref 39.
  • 102
    • 45749086894 scopus 로고    scopus 로고
    • Forming bond C-C distances, TSI: 2.18Å; TSII: 2.33Å; TSIII: 2.39Å.
    • Forming bond C-C distances, TSI: 2.18Å; TSII: 2.33Å; TSIII: 2.39Å.
  • 104
    • 85021596191 scopus 로고
    • For X-Ray evidence of a H-bond network in a tetrabutyl ammonium cation, see
    • For X-Ray evidence of a H-bond network in a tetrabutyl ammonium cation, see: Reetz, M. T.; Hüette, S.; Goddard, R. J. Am. Chem. Soc. 1993, 115, 9339-9340.
    • (1993) J. Am. Chem. Soc , vol.115 , pp. 9339-9340
    • Reetz, M.T.1    Hüette, S.2    Goddard, R.3


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