메뉴 건너뛰기




Volumn 107, Issue 48, 2010, Pages 20655-20660

Lewis base catalysis of bromo- and iodolactonization, and cycloetherification

Author keywords

Halocyclofunctionalization; Halogenation

Indexed keywords

LEWIS BASE;

EID: 78650580819     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1005296107     Document Type: Article
Times cited : (219)

References (35)
  • 1
    • 2542478906 scopus 로고    scopus 로고
    • Halo- and selenolactonization: The two major strategies for cyclofunctionalization
    • Ranganathan S, Muraleedharan KM, Vaish NK, Jayaraman N (2004) Halo- and selenolactonization: the two major strategies for cyclofunctionalization. Tetrahedron 60:5273-5308.
    • (2004) Tetrahedron , vol.60 , pp. 5273-5308
    • Ranganathan, S.1    Muraleedharan, K.M.2    Vaish, N.K.3    Jayaraman, N.4
  • 2
  • 3
    • 0001657273 scopus 로고
    • Sterocontrolled cyclofunctionalizations of double bonds through heterocyclic intermediates
    • Cardillo G, Orena M (1990) Sterocontrolled cyclofunctionalizations of double bonds through heterocyclic intermediates. Tetrahedron 46:3321-3408.
    • (1990) Tetrahedron , vol.46 , pp. 3321-3408
    • Cardillo, G.1    Orena, M.2
  • 4
    • 37049112036 scopus 로고
    • Synthesis and synthetic utility of halolactones
    • Dowle MD, Davies DI (1979) Synthesis and synthetic utility of halolactones. Chem Soc Rev 8:171-197.
    • (1979) Chem Soc Rev , vol.8 , pp. 171-197
    • Dowle, M.D.1    Davies, D.I.2
  • 5
    • 4444307147 scopus 로고    scopus 로고
    • Iodine electrophiles in stereoselective reactions: Recent developments and synthetic applications
    • French AN, Bissmire S, Wirth T (2004) Iodine electrophiles in stereoselective reactions: recent developments and synthetic applications. Chem Soc Rev 33:354-362.
    • (2004) Chem Soc Rev , vol.33 , pp. 354-362
    • French, A.N.1    Bissmire, S.2    Wirth, T.3
  • 6
    • 70349972014 scopus 로고    scopus 로고
    • Intramolecular haloetherification and transannular hydroxycyclization of alkenes A synthetic methodology to obtain polycyclic ethers and amines
    • Montana AM, Batalla C, Barcia JA (2009) Intramolecular haloetherification and transannular hydroxycyclization of alkenes. A synthetic methodology to obtain polycyclic ethers and amines. Curr Org Chem 13:919-938.
    • (2009) Curr Org Chem , vol.13 , pp. 919-938
    • Montana, A.M.1    Batalla, C.2    Barcia, J.A.3
  • 7
    • 38849097138 scopus 로고    scopus 로고
    • Asymmetric iodocyclization catalyzed by salen-CrIIICl: Its synthetic application to swainsonine
    • Kwon HY, Park CM, Lee SB, Youn J-H, Kang SH (2008) Asymmetric iodocyclization catalyzed by salen-CrIIICl: its synthetic application to swainsonine. Chemistry-A European Journal 14:1023-1028.
    • (2008) Chemistry-A European Journal , vol.14 , pp. 1023-1028
    • Kwon, H.Y.1    Park, C.M.2    Lee, S.B.3    Youn, J.-H.4    Kang, S.H.5
  • 8
    • 1842638312 scopus 로고    scopus 로고
    • Enantioselective iodolactonization catalyzed by chiral quaternary ammonium salts derived from cinchonidine
    • Wang M, et al. (2004) Enantioselective iodolactonization catalyzed by chiral quaternary ammonium salts derived from cinchonidine. J Org Chem 69:2874-2876.
    • (2004) J Org Chem , vol.69 , pp. 2874-2876
    • Wang, M.1
  • 10
    • 77949791576 scopus 로고    scopus 로고
    • Enantioselective bromolactonization of conjugated (Z)-enynes
    • Zhang W, et al. (2010) Enantioselective bromolactonization of conjugated (Z)-enynes. J Am Chem Soc 132:3664-3665.
    • (2010) J Am Chem Soc , vol.132 , pp. 3664-3665
    • Zhang, W.1
  • 11
    • 0001571271 scopus 로고    scopus 로고
    • A new palladium(II)-catalyzed asymmetric chlorohydrin synthesis
    • El-Qisairi A, Hamed O, Henry PM (1998) A new palladium(II)-catalyzed asymmetric chlorohydrin synthesis. J Org Chem 63:2790-2791.
    • (1998) J Org Chem , vol.63 , pp. 2790-2791
    • El-Qisairi, A.1    Hamed, O.2    Henry, P.M.3
  • 12
    • 0038178336 scopus 로고    scopus 로고
    • New palladium(II)-catalyzed asymmetric 1,2-dibromo synthesis
    • El-Qisairi AK, et al. (2003) New palladium(II)-catalyzed asymmetric 1,2-dibromo synthesis. Org Lett 5:439-441.
    • (2003) Org Lett , vol.5 , pp. 439-441
    • El-Qisairi, A.K.1
  • 13
    • 34447542393 scopus 로고    scopus 로고
    • An approach to enantioselective 5-endo halo-lactonization reactions
    • Garnier JM, Robin S, Rousseau G (2007) An approach to enantioselective 5-endo halo-lactonization reactions. Eur J Org Chem 2007:3281-3291.
    • (2007) Eur J Org Chem , vol.2007 , pp. 3281-3291
    • Garnier, J.M.1    Robin, S.2    Rousseau, G.3
  • 14
    • 25444442832 scopus 로고    scopus 로고
    • Iodine monochloride-amine complexes: An experimental and computational approach to new chiral electrophiles
    • Haas J, Bissmire S, Wirth T (2005) Iodine monochloride-amine complexes: an experimental and computational approach to new chiral electrophiles. Chemistry-A European Journal 11:5777-5785.
    • (2005) Chemistry-A European Journal , vol.11 , pp. 5777-5785
    • Haas, J.1    Bissmire, S.2    Wirth, T.3
  • 15
    • 33847218271 scopus 로고    scopus 로고
    • Enantioselective halocyclization of polyprenoids induced by nucleophilic phosphoramidites
    • Sakakura A, Ukai A, Ishihara K (2007) Enantioselective halocyclization of polyprenoids induced by nucleophilic phosphoramidites. Nature 445:900-903.
    • (2007) Nature , vol.445 , pp. 900-903
    • Sakakura, A.1    Ukai, A.2    Ishihara, K.3
  • 16
    • 0000036785 scopus 로고
    • Stable bromonium and iodonium ions of the hindered olefins adamantylideneadamantane and Bicyclo[3.3.1]nonylidenebicyclo[3.3.1]nonane. X-ray structure, transfer of positive halogens to acceptor olefins, and ab initio studies
    • Brown RS, et al. (1994) Stable bromonium and iodonium ions of the hindered olefins adamantylideneadamantane and Bicyclo[3.3.1]nonylidenebicyclo[3. 3.1]nonane. X-ray structure, transfer of positive halogens to acceptor olefins, and ab initio studies. J Am Chem Soc 116:2448-2456.
    • (1994) J Am Chem Soc , vol.116 , pp. 2448-2456
    • Brown, R.S.1
  • 17
    • 0001356401 scopus 로고    scopus 로고
    • + transfer from the halonium ions of adamantylideneadamantane to acceptor olefins. halocyclization of 1,?-alkenols and alkenoic acids proceeds via reversibly formed intermediates
    • + transfer from the halonium ions of adamantylideneadamantane to acceptor olefins. halocyclization of 1,?-alkenols and alkenoic acids proceeds via reversibly formed intermediates. J Org Chem 61:962-968.
    • (1996) J Org Chem , vol.61 , pp. 962-968
    • Neverov, A.A.1    Brown, R.S.2
  • 18
    • 0001349866 scopus 로고    scopus 로고
    • Investigation of the early steps in electrophilic bromination through the study of the reaction with sterically encumbered olefins
    • Brown RS (1997) Investigation of the early steps in electrophilic bromination through the study of the reaction with sterically encumbered olefins. Acc Chem Res 30:131-137.
    • (1997) Acc Chem Res , vol.30 , pp. 131-137
    • Brown, R.S.1
  • 19
    • 77950341605 scopus 로고    scopus 로고
    • On the absolute configurational stability of bromonium and chloronium ions
    • Denmark SE, Burk MT, Hoover AJ (2010) On the absolute configurational stability of bromonium and chloronium ions. J Am Chem Soc 132:1232-1233.
    • (2010) J Am Chem Soc , vol.132 , pp. 1232-1233
    • Denmark, S.E.1    Burk, M.T.2    Hoover, A.J.3
  • 21
    • 33846107564 scopus 로고    scopus 로고
    • Dimethylformamide, dimethylacetamide, and tetramethylguanidine as nucleophilic organocatalysts for the transfer of electrophilic bromine from N-bromosuccinimide to alkenes
    • Ahmad SM, Braddock DC, Cansell G, Hermitage SA (2007) Dimethylformamide, dimethylacetamide, and tetramethylguanidine as nucleophilic organocatalysts for the transfer of electrophilic bromine from N-bromosuccinimide to alkenes. Tetrahedron Lett 48:915-918.
    • (2007) Tetrahedron Lett , vol.48 , pp. 915-918
    • Ahmad, S.M.1    Braddock, D.C.2    Cansell, G.3    Hermitage, S.A.4
  • 22
    • 33947135438 scopus 로고    scopus 로고
    • Reaction of imines with N-iodosuccinimide (NIS): Unexpected formation of stable 1:1 complexes
    • Castellote I, et al. (2007) Reaction of imines with N-iodosuccinimide (NIS): unexpected formation of stable 1:1 complexes. Chem Commun 43:1281-1283.
    • (2007) Chem Commun , vol.43 , pp. 1281-1283
    • Castellote, I.1
  • 23
    • 67849091011 scopus 로고    scopus 로고
    • DABCO-catalyzed 1,4-bromolactonization of conjugated enynes: Highly stereoselective formation of a stereogenic center and an axially chiral allene
    • Zhang W, Xu H, Xu H, Tang W (2009) DABCO-catalyzed 1,4-bromolactonization of conjugated enynes: highly stereoselective formation of a stereogenic center and an axially chiral allene. J Am Chem Soc 131:3832-3833.
    • (2009) J Am Chem Soc , vol.131 , pp. 3832-3833
    • Zhang, W.1    Xu, H.2    Xu, H.3    Tang, W.4
  • 24
    • 0000012312 scopus 로고
    • Olefin cyclization processes that form carbon-heteroatom bonds
    • ed JD Morrison (Academic, FL)
    • Bartlett PA (1984) Olefin cyclization processes that form carbon-heteroatom bonds. Asymmetric Synthesis, ed JD Morrison (Academic, FL), 3, pp 411-454.
    • (1984) Asymmetric Synthesis , vol.3 , pp. 411-454
    • Bartlett, P.A.1
  • 25
    • 0001085035 scopus 로고
    • Regioselectivity of the halolactonization of ?,d-unsaturated acids
    • Snider BB, Johnston MI (1985) Regioselectivity of the halolactonization of ?,d-unsaturated acids. Tetrahedron 26:5497-5500.
    • (1985) Tetrahedron , vol.26 , pp. 5497-5500
    • Snider, B.B.1    Johnston, M.I.2
  • 26
    • 0001505949 scopus 로고
    • Stereoselective epoxidation of acyclic olefinic carboxylic acids via iodolactonization
    • Bartlett PA, Myerson J (1978) Stereoselective epoxidation of acyclic olefinic carboxylic acids via iodolactonization. J Am Chem Soc 100:3950-3952.
    • (1978) J Am Chem Soc , vol.100 , pp. 3950-3952
    • Bartlett, P.A.1    Myerson, J.2
  • 27
    • 0000237619 scopus 로고
    • An interpretation of the chemical behavior of five- and six-membered ring compounds
    • Brown HC, Brewster JH, Shechter H (1954) An interpretation of the chemical behavior of five- and six-membered ring compounds. J Am Chem Soc 76:467-474.
    • (1954) J Am Chem Soc , vol.76 , pp. 467-474
    • Brown, H.C.1    Brewster, J.H.2    Shechter, H.3
  • 28
    • 41049092939 scopus 로고
    • Charge transfer complexes of hexamethylphosphoramide chalcogenides
    • Bruno P, Caselli M, Fragale C, Magrino S (1977) Charge transfer complexes of hexamethylphosphoramide chalcogenides. J Inorg Nucl Chem 39:1757-1759.
    • (1977) J Inorg Nucl Chem , vol.39 , pp. 1757-1759
    • Bruno, P.1    Caselli, M.2    Fragale, C.3    Magrino, S.4
  • 29
    • 0040833669 scopus 로고
    • Correlation between the Dipole moments and thermodynamical data of the iodine complexes with organic oxides, sulfides, and selenides
    • Glera J, Sobczyk L, Paetroldt R (1980) Correlation between the Dipole moments and thermodynamical data of the iodine complexes with organic oxides, sulfides, and selenides. J Phys Chem 84:2602-2605.
    • (1980) J Phys Chem , vol.84 , pp. 2602-2605
    • Glera, J.1    Sobczyk, L.2    Paetroldt, R.3
  • 30
    • 46149108743 scopus 로고
    • Iodolactonization and dihydroxylation of 5-phenyl pentenoic acids (in French
    • Julia MM, Guy-Roualt A (1964) Iodolactonization and dihydroxylation of 5-phenyl pentenoic acids (in French). C R Hebd Seances Acad Sci 258:3728-3730.
    • (1964) C R Hebd Seances Acad Sci , vol.258 , pp. 3728-3730
    • Julia, M.M.1    Guy-Roualt, A.2
  • 31
    • 1542739713 scopus 로고
    • The ionization constant and rate of hydrolysis of succinimide
    • Walton H, Schilt A (1952) The ionization constant and rate of hydrolysis of succinimide. J Am Chem Soc 74:4995-4996.
    • (1952) J Am Chem Soc , vol.74 , pp. 4995-4996
    • Walton, H.1    Schilt, A.2
  • 32
    • 0035981605 scopus 로고    scopus 로고
    • Thermodynamic quantities for the ionization reactions of buffers
    • Goldberg RN (1999) Thermodynamic quantities for the ionization reactions of buffers. J Phys Chem Ref Data 31:231-370.
    • (1999) J Phys Chem Ref Data , vol.31 , pp. 231-370
    • Goldberg, R.N.1
  • 33
    • 0000099175 scopus 로고
    • Acid-base properties of organic solvents
    • Bagno A, Scorrano G (1988) Acid-base properties of organic solvents. J Am Chem Soc 110:4577-4582.
    • (1988) J Am Chem Soc , vol.110 , pp. 4577-4582
    • Bagno, A.1    Scorrano, G.2
  • 34
    • 0029759834 scopus 로고    scopus 로고
    • Free radical chemistry of lactones: Ring contractions and expansions
    • Crich D, Beckwith ALJ, Filzen GF, Longmore RW (1996) Free radical chemistry of lactones: ring contractions and expansions. J Am Chem Soc 118:7422-7423.
    • (1996) J Am Chem Soc , vol.118 , pp. 7422-7423
    • Crich, D.1    Alj, B.2    Filzen, G.F.3    Longmore, R.W.4
  • 35
    • 0015358739 scopus 로고
    • Cis- and trans-3-Methylamino-2-phenyltetrahydropyran
    • Galpin DR, Bobbink SR, Ary TE (1972) cis- and trans-3-Methylamino-2- phenyltetrahydropyran. J Pharm Sci 61:963-964.
    • (1972) J Pharm Sci , vol.61 , pp. 963-964
    • Galpin, D.R.1    Bobbink, S.R.2    Ary, T.E.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.