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Volumn 42, Issue 5, 2012, Pages 1685-1694

Diastereoselective Michael reaction of chiral nickel(II) glycinate with nitroalkenes for asymmetric synthesis of β-substituted α,γ- diaminobutyric acid derivatives in water

Author keywords

Asymmetric synthesis; Diaminobutyric acids; Michael reaction; Nickel(II) glycinate

Indexed keywords

ALKENE DERIVATIVE; ALPHA,GAMMA DIAMINOBUTYRIC ACID DERIVATIVE; AMINO ACID; BROMINE DERIVATIVE; NICKEL COMPLEX; NICKEL GLYCINATE; NITROALKENE DERIVATIVE; TETRABUTYL AMMONIUM BROMIDE; UNCLASSIFIED DRUG; WATER;

EID: 84862755098     PISSN: 09394451     EISSN: 14382199     Source Type: Journal    
DOI: 10.1007/s00726-011-0870-x     Document Type: Article
Times cited : (13)

References (30)
  • 2
    • 33749244809 scopus 로고    scopus 로고
    • Three generations of α,γ-diaminobutyric acid modified poly(propyleneimine) dendrimers and their cisplatin-type platinum complexes
    • DOI 10.1016/j.jbbm.2006.02.006, PII S0165022X06000352, Proceedings of the 8th International Symposium on Instrumental Analysis
    • Bellis E, Hajba L, Kovacs B, Sandor K, Kollar L, Kokotos G (2006) Three generations of a,c-diaminobutyric acid modified poly (propyleneimine) dendrimers and their cisplatin-type platinum complexes. J Biochem Biophys Methods 69:151-161 (Pubitemid 44486419)
    • (2006) Journal of Biochemical and Biophysical Methods , vol.69 , Issue.1-2 , pp. 151-161
    • Bellis, E.1    Hajba, L.2    Kovacs, B.3    Sandor, K.4    Kollar, L.5    Kokotos, G.6
  • 4
    • 0035936788 scopus 로고    scopus 로고
    • Michael addition reactions between chiral Ni(II) complex of glycine and 3-(trans-enoyl)oxazolidin-2-ones. A case of electron donor - Acceptor attractive interaction-controlled face diastereoselectivity
    • DOI 10.1021/jo0014865
    • Cai C, Soloshonok VA, Hruby VJ (2001) Michael addition reactions between chiral Ni(II) complex of glycine and 3-(trans-enoyl)oxazolidin- 2-ones. A case of electron donor-acceptor attractive interaction-controlled face diastereoselectivity. J Org Chem 66:1339-1350 (Pubitemid 32202317)
    • (2001) Journal of Organic Chemistry , vol.66 , Issue.4 , pp. 1339-1350
    • Cai, C.1    Soloshonok, V.A.2    Hruby, V.J.3
  • 5
    • 4344655353 scopus 로고    scopus 로고
    • Application of (S)- and (R)-methyl pyroglutamates as inexpensive, yet highly efficient chiral auxiliaries in the asymmetric Michael addition reactions
    • DOI 10.1016/j.tetlet.2004.07.096, PII S0040403904015953
    • Cai C, Yamada T, Tiwari R, Hruby VJ, Soloshonok VA (2004) Application of (S)- and (R)-methyl pyroglutamates as inexpensive, yet highly efficient chiral auxiliaries in the asymmetric Michael addition reactions. Tetrahedron Lett 45:6855-6858 (Pubitemid 39140577)
    • (2004) Tetrahedron Letters , vol.45 , Issue.37 , pp. 6855-6858
    • Cai, C.1    Yamada, T.2    Tiwari, R.3    Hruby, V.J.4    Soloshonok, V.A.5
  • 6
    • 33750428967 scopus 로고    scopus 로고
    • α,γ-diamino acids: Asymmetric synthesis of new constrained 6-amino-3-azabicyclo[3.2.1]octane-6-carboxylic acids
    • DOI 10.1021/jo061391o
    • Caputo F, Cattaneo C, Clerici F, Gelmi ML, Pellegrino S (2006) a, c-diamino acids: asymmetric synthesis of new constrained 6-amino-3-azabicyclo[3. 2.1]octane-6-carboxylic acids. J Org Chem 71:8467-8472 (Pubitemid 44656037)
    • (2006) Journal of Organic Chemistry , vol.71 , Issue.22 , pp. 8467-8472
    • Caputo, F.1    Cattaneo, C.2    Clerici, F.3    Gelmi, M.L.4    Pellegrino, S.5
  • 7
    • 2342616085 scopus 로고    scopus 로고
    • Effects on cocaine and food self-administration of (+)-HA-966, a partial agonist at the glycine/NMDA modulatory site, in rats
    • DOI 10.1007/s00213-003-1703-8
    • Cervo L, Cocco A, Carnovali F (2004) Effects on cocaine and food self-administration of (?)-HA-966, a partial agonist at the glycine/NMDA modulatory site, in rats. Psychopharmacology (Berl) 173:124-131 (Pubitemid 38591156)
    • (2004) Psychopharmacology , vol.173 , Issue.1-2 , pp. 124-131
    • Cervo, L.1    Cocco, A.2    Carnovali, F.3
  • 10
    • 20444444681 scopus 로고    scopus 로고
    • Unique michael addition-initiated domino reaction for the stereoselective synthesis of functionalized macrolactones from α-nitroketones in water
    • DOI 10.1021/ol0505860
    • Giorgi G, Miranda S, Lopez-Alvarado P, Avendano C, Rodriguez J, Menendez JC (2005) Unique Michael addition-initiated domino reaction for the stereoselective synthesis of functionalized macrolactones from a-nitroketones in water. Org Lett 7:2197-2200 (Pubitemid 40826083)
    • (2005) Organic Letters , vol.7 , Issue.11 , pp. 2197-2200
    • Giorgi, G.1    Miranda, S.2    Lopez-Alvarado, P.3    Avendano, C.4    Rodriguez, J.5    Menendez, J.C.6
  • 11
    • 0027294037 scopus 로고
    • Lack of effect of L-687,414 (+)-cis-4-methyl-HA-966), an NMDA receptor antagonist acting at the glycine site, on cerebral glucose metabolism and cortical neuronal morphology
    • Hargreaves RJ, Rigby M, Smith D, Hill RG (1993) Lack of effect of L-687, 414 ((?)-cis-4-methyl-HA-966), an NMDA receptor antagonist acting at the glycine site, on cerebral glucose metabolism and cortical neuronal morphology. Br J Pharmacol 110:36-42 (Pubitemid 23257755)
    • (1993) British Journal of Pharmacology , vol.110 , Issue.1 , pp. 36-42
    • Hargreaves, R.J.1    Rigby, M.2    Smith, D.3    Hill, R.G.4
  • 12
    • 34447131678 scopus 로고    scopus 로고
    • Reactions of C-H bonds in water
    • DOI 10.1021/cr050980b
    • Herrerias CI, Yao X, Li Z, Li CJ (2007) Reactions of C-H bonds in water. Chem Rev 107:2546-2562 (Pubitemid 47033770)
    • (2007) Chemical Reviews , vol.107 , Issue.6 , pp. 2546-2562
    • Herrerias, C.I.1    Yao, X.2    Li, Z.3    Li, C.-J.4
  • 13
    • 64549086375 scopus 로고    scopus 로고
    • Diastereoselective synthesis of b-substituted - A,c-diaminobutyric acids and pyrrolidines containing multichiral centers
    • Huang Y, Li Q, Liu TL, Xu PF (2009) Diastereoselective synthesis of b-substituted-a,c-diaminobutyric acids and pyrrolidines containing multichiral centers. J Org Chem 74:1252-1258
    • (2009) J Org Chem , vol.74 , pp. 1252-1258
    • Huang, Y.1    Li, Q.2    Liu, T.L.3    Xu, P.F.4
  • 14
    • 43749099439 scopus 로고    scopus 로고
    • Identification of a novel β-replacement reaction in the biosynthesis of 2,3-diaminobutyric acid in peptidylnucleoside mureidomycin A
    • DOI 10.1039/b802585a
    • Lam WH, Rychli K, Bugg TD (2008) Identification of a novel b-replacement reaction in the biosynthesis of 2,3-diaminobutyric acid in peptidylnucleoside mureidomycin A. Org Biomol Chem 6:1912-1917 (Pubitemid 351693235)
    • (2008) Organic and Biomolecular Chemistry , vol.6 , Issue.11 , pp. 1912-1917
    • Lam, W.-H.1    Rychli, K.2    Bugg, T.D.H.3
  • 15
    • 24044470646 scopus 로고    scopus 로고
    • Organic reactions in aqueous media with a focus on carbon-carbon bond formations: A decade update
    • Li CJ (2005) Organic reactions in aqueous media with a focus on carbon-carbon bond formations: a decade update. Chem Rev 105:3095-3165
    • (2005) Chem Rev , vol.105 , pp. 3095-3165
    • Li, C.J.1
  • 16
    • 33645383062 scopus 로고    scopus 로고
    • Organic chemistry in water
    • DOI 10.1039/b507207g
    • Li CJ, Chen L (2006) Organic chemistry in water. Chem Soc Rev 35:68-82 (Pubitemid 43485014)
    • (2006) Chemical Society Reviews , vol.35 , Issue.1 , pp. 68-82
    • Li, C.-J.1    Chen, L.2
  • 17
    • 0036703508 scopus 로고    scopus 로고
    • Stereoselective organic reactions in water
    • DOI 10.1021/cr010122p
    • Lindstrom UM (2002) Stereoselective organic reactions in water. Chem Rev 102:2751-2772 (Pubitemid 35377630)
    • (2002) Chemical Reviews , vol.102 , Issue.8 , pp. 2751-2772
    • Lindstrom, U.M.1
  • 18
    • 33745048479 scopus 로고    scopus 로고
    • 2-symmetric tridentate bis(oxazoline) and bis(thiazoline) zinc complexes
    • DOI 10.1021/ja0604008
    • Lu SF, Du DM, Xu J, Zhang SW (2006) Asymmetric Michael addition of nitroalkanes to nitroalkenes catalyzed by C2- symmetric tridentate bis(oxazoline) and bis(thiazoline) zinc complexes. J Am Chem Soc 128:7418-7419 (Pubitemid 43877497)
    • (2006) Journal of the American Chemical Society , vol.128 , Issue.23 , pp. 7418-7419
    • Lu, S.-F.1    Du, D.-M.2    Xu, J.3    Zhang, S.-W.4
  • 19
    • 58949092249 scopus 로고    scopus 로고
    • Asymmetric Michael addition mediated by novel cinchona alkaloid-derived bifunctional catalysts containing sulfonamides
    • Luo J, Xu LW, Hay RA, Lu Y (2009) Asymmetric Michael addition mediated by novel cinchona alkaloid-derived bifunctional catalysts containing sulfonamides. Org Lett 11:437-440
    • (2009) Org Lett , vol.11 , pp. 437-440
    • Luo, J.1    Xu, L.W.2    Hay, R.A.3    Lu, Y.4
  • 20
    • 0034674250 scopus 로고    scopus 로고
    • A practical asymmetric synthesis of enantiomerically pure 3-substituted pyroglutamic acids and related compounds
    • DOI 10.1002/1521-3773(20000616)39:12<2172::AID-ANIE2172>3.0.CO;2-0
    • Soloshonok VA, Cai C, Hruby VJ (2000) A practical asymmetric synthesis of enantiomerically pure 3-substituted pyroglutamic acids and related compounds. Angew Chem Int Ed 39:2172-2175 (Pubitemid 30435623)
    • (2000) Angewandte Chemie - International Edition , vol.39 , Issue.12 , pp. 2172-2175
    • Soloshonok, V.A.1    Cai, C.2    Hruby, V.J.3
  • 21
    • 0035825745 scopus 로고    scopus 로고
    • Asymmetric Synthesis of α,β-Dialkyl-α-phenylalanines via Direct Alkylation of a Chiral Alanine Derivative with Racemic α-Alkylbenzyl Bromides. A Case of High Enantiomer Differentiation at Room Temperature
    • DOI 10.1021/ol000330o
    • Soloshonok VA, Tang X, Hruby VJ, Van Meervelt L (2001) Asymmetric synthesis of a, b-dialkyl-a-phenylalanines via direct alkylation of a chiral alanine derivative with racemic a-alkylbenzyl bromides. A case of high enantiomer differentiation at room temperature. Org Lett 3:341-343 (Pubitemid 33692990)
    • (2001) Organic Letters , vol.3 , Issue.3 , pp. 341-343
    • Soloshonok, V.A.1    Tang, X.2    Hruby, V.J.3    Van Meervelt, L.4
  • 22
    • 8544228333 scopus 로고    scopus 로고
    • Asymmetric synthesis of enantiomerically pure 4-aminoglutamic acids via methylenedimerization of chiral glycine equivalents with dichloromethane under operationally convenient conditions
    • DOI 10.1016/j.tetlet.2004.10.111, PII S0040403904023536
    • Taylor SM, Yamada T, Ueki H, Soloshonok VA (2004) Asymmetric synthesis of enantiomerically pure 4-aminoglutamic acids via methylenedimerization of chiral glycine equivalents with dichloromethane under operationally convenient conditions. Tetrahedron Lett 45:9159-9162 (Pubitemid 39491137)
    • (2004) Tetrahedron Letters , vol.45 , Issue.50 , pp. 9159-9162
    • Taylor, S.M.1    Yamada, T.2    Ueki, H.3    Soloshonok, V.A.4
  • 23
    • 33846701129 scopus 로고    scopus 로고
    • Unanticipated differences between α- and γ-diaminobutyric acid-linked hairpin polyamide-alkylator conjugates
    • DOI 10.1093/nar/gkl1025
    • Tsai SM, Farkas ME, Chou CJ, Gottesfeld JM, Dervan PB (2007) Unanticipated differences between a- and c-diaminobutyric acidlinked hairpin polyamide-alkylator conjugates. Nucleic Acids Res 35:307-316 (Pubitemid 46189855)
    • (2007) Nucleic Acids Research , vol.35 , Issue.1 , pp. 307-316
    • Tsai, S.M.1    Farkas, M.E.2    Chou, C.J.3    Gottesfeld, J.M.4    Dervan, P.B.5
  • 24
    • 70449555921 scopus 로고    scopus 로고
    • Chiral calcium catalysts with neutral coordinative ligands: Enantioselective 1,4- addition reactions of 1,3-dicarbonyl compounds to nitroalkenes
    • Tsubogo T, Yamashita Y, Kobayashi S (2009) Chiral calcium catalysts with neutral coordinative ligands: enantioselective 1,4- addition reactions of 1,3-dicarbonyl compounds to nitroalkenes. Angew Chem Int Ed 48:9117-9120
    • (2009) Angew Chem Int Ed , vol.48 , pp. 9117-9120
    • Tsubogo, T.1    Yamashita, Y.2    Kobayashi, S.3
  • 26
    • 33947605163 scopus 로고    scopus 로고
    • Highly enantioselective water-compatible organocatalyst for Michael reaction of ketones to nitroolefins
    • Vishnumaya Singh VK (2007) Highly enantioselective water-compatible organocatalyst for Michael reaction of ketones to nitroolefins. Org Lett 9:1117-1119
    • (2007) Org Lett , vol.9 , pp. 1117-1119
    • Vishnumaya Singh, V.K.1
  • 27
    • 34447102708 scopus 로고    scopus 로고
    • A green chemistry approach to asymmetric catalysis: Solvent-free and highly concentrated reactions
    • DOI 10.1021/cr0509556
    • Walsh PJ, Li H, De Parrodi CA (2007) A green chemistry approach to asymmetric catalysis: solvent-free and highly concentrated reactions. Chem Rev 107:2503-2545 (Pubitemid 47029099)
    • (2007) Chemical Reviews , vol.107 , Issue.6 , pp. 2503-2545
    • Walsh, P.J.1    Li, H.2    Anaya De Parrodi, C.3
  • 28
    • 55249094794 scopus 로고    scopus 로고
    • Highly enantio- and diastereoselective mannich reactions of chiral Ni(II) glycinates with amino sulfones. Efficient asymmetric synthesis of aromatic a,b-diamino acids
    • Wang J, Shi T, Deng GH, Jiang H, Liu H (2008) Highly enantio- and diastereoselective mannich reactions of chiral Ni(II) glycinates with amino sulfones. Efficient asymmetric synthesis of aromatic a,b-diamino acids. J Org Chem 73:8563-8570
    • (2008) J Org Chem , vol.73 , pp. 8563-8570
    • Wang, J.1    Shi, T.2    Deng, G.H.3    Jiang, H.4    Liu, H.5
  • 29
    • 33746290157 scopus 로고    scopus 로고
    • A highly enantio- and diastereoselective Cu-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with nitroalkenes
    • DOI 10.1002/anie.200503672
    • Yan X-X, Peng Q, Zhang Y, Zhang K, Hong W, Hou XL, Wu YD (2006) A highly enantio- and diastereoselective Cu-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with nitroalkenes. Angew Chem Int Ed 45:1979-1983 (Pubitemid 44105233)
    • (2006) Angewandte Chemie - International Edition , vol.45 , Issue.12 , pp. 1979-1983
    • Yan, X.-X.1    Peng, Q.2    Zhang, Y.3    Zhang, K.4    Hong, W.5    Hou, X.-L.6    Wu, Y.-D.7
  • 30
    • 70349898291 scopus 로고    scopus 로고
    • An efficient synthesis of chiral diamines with rigid backbones: Application in enantioselective Michael addition of malonates to nitroalkenes
    • Zhu Q, Huang H, Shi D, Shen Z, Xia C (2009) An efficient synthesis of chiral diamines with rigid backbones: application in enantioselective Michael addition of malonates to nitroalkenes. Org Lett 11:4536-4539
    • (2009) Org Lett , vol.11 , pp. 4536-4539
    • Zhu, Q.1    Huang, H.2    Shi, D.3    Shen, Z.4    Xia, C.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.