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Volumn 9, Issue 23, 2007, Pages 4901-4904

An organocatalytic oxidative coupling strategy for the direct synthesis of arylated quaternary stereogenic centers

Author keywords

[No Author keywords available]

Indexed keywords

BENZOQUINONE; BENZOQUINONE DERIVATIVE; BIOLOGICAL PRODUCT; CATECHOL; CATECHOL DERIVATIVE; ORGANIC COMPOUND; PHENYLACETIC ACID DERIVATIVE; PHENYLACETIC ACID ETHYL ESTER; UNCLASSIFIED DRUG;

EID: 36348935166     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702277v     Document Type: Article
Times cited : (31)

References (50)
  • 1
    • 36348992091 scopus 로고    scopus 로고
    • Steidle, W.; Dengel, F. GB1101479, 1968.
    • (a) Steidle, W.; Dengel, F. GB1101479, 1968.
  • 3
    • 0023115108 scopus 로고
    • For a stereospecific synthesis, see
    • (c) For a stereospecific synthesis, see: Theodore, L. J.; Nelson, W. L. J. Org. Chem. 1987, 52, 1309.
    • (1987) J. Org. Chem , vol.52 , pp. 1309
    • Theodore, L.J.1    Nelson, W.L.2
  • 6
    • 0346433486 scopus 로고    scopus 로고
    • Other examples include the Amaryllidaceae alkaloid family; for a review, see
    • Other examples include the Amaryllidaceae alkaloid family; for a review, see: Jin, Z. Nat. Prod. Rep. 2003, 20, 606.
    • (2003) Nat. Prod. Rep , vol.20 , pp. 606
    • Jin, Z.1
  • 7
  • 8
    • 0033620428 scopus 로고    scopus 로고
    • For asymmetric total syntheses, see
    • (b) For asymmetric total syntheses, see: Degnan, A. P.; Meyers, A. I. J. Am. Chem. Soc. 1999, 121, 2762.
    • (1999) J. Am. Chem. Soc , vol.121 , pp. 2762
    • Degnan, A.P.1    Meyers, A.I.2
  • 9
    • 32644439884 scopus 로고    scopus 로고
    • For a review on the enantioselective construction of all carbon quaternary centers, see
    • For a review on the enantioselective construction of all carbon quaternary centers, see: Trost, B. M.; Jiang, C. Synthesis 2006, 3, 369.
    • (2006) Synthesis , vol.3 , pp. 369
    • Trost, B.M.1    Jiang, C.2
  • 10
    • 33846027862 scopus 로고    scopus 로고
    • For the use of Friedel-Crafts alkylations to form arylated quaternary centers, see: a
    • For the use of Friedel-Crafts alkylations to form arylated quaternary centers, see: (a) Grundl, M. A.; Kaster, A.; Beaulieu, E. D.; Trauner, D. Org. Lett. 2006, 8, 5429.
    • (2006) Org. Lett , vol.8 , pp. 5429
    • Grundl, M.A.1    Kaster, A.2    Beaulieu, E.D.3    Trauner, D.4
  • 12
    • 4043123499 scopus 로고    scopus 로고
    • For a review, see:, 3453 and references 39-44 therein
    • (a) For a review, see: Tietze, L. F.; Ila, H.; Bell, H. P. Chem. Rev. 2004, 104, 3453 and references 39-44 therein.
    • (2004) Chem. Rev , vol.104
    • Tietze, L.F.1    Ila, H.2    Bell, H.P.3
  • 14
    • 8444227142 scopus 로고    scopus 로고
    • For the application of intramolecular Heck coupling in synthesis, see: c
    • For the application of intramolecular Heck coupling in synthesis, see: (c) Tietze, L. F.; Wiegand, J. M.; Vock, C. A. Eur. J. Org. Chem. 2004, 20, 4107.
    • (2004) Eur. J. Org. Chem , vol.20 , pp. 4107
    • Tietze, L.F.1    Wiegand, J.M.2    Vock, C.A.3
  • 23
    • 33845579450 scopus 로고    scopus 로고
    • For Cu-catalyzed coupling, see
    • For Cu-catalyzed coupling, see: Xie, X.; Chen, Y.; Ma, D. J. Am. Chem. Soc. 2006, 128, 16050.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 16050
    • Xie, X.1    Chen, Y.2    Ma, D.3
  • 24
    • 34250613134 scopus 로고    scopus 로고
    • For selected reviews on organocatalysis, see: a
    • For selected reviews on organocatalysis, see: (a) Tsogoeva, S. B. Eur. J. Org. Chem. 2007, 11, 1701.
    • (2007) Eur. J. Org. Chem , vol.11 , pp. 1701
    • Tsogoeva, S.B.1
  • 29
    • 36348949813 scopus 로고    scopus 로고
    • Acc. Chem. Res. 2004, 37, special issue on organocatalysis.
    • (f) Acc. Chem. Res. 2004, 37, special issue on organocatalysis.
  • 32
    • 36348932915 scopus 로고    scopus 로고
    • o-Benzoquinones are notoriously unstable, and as a result (in contrast to p-quinones), examples of their use as Michael acceptors, particularly toward carbon-centered nucleophiles, are rare. For additions of allylstannanes, see: (a) Maruyama, K.; Takuwa, A.; Naruta, Y.; Satao, K.; Soga, O. Chem. Lett. 1981, 47.
    • o-Benzoquinones are notoriously unstable, and as a result (in contrast to p-quinones), examples of their use as Michael acceptors, particularly toward carbon-centered nucleophiles, are rare. For additions of allylstannanes, see: (a) Maruyama, K.; Takuwa, A.; Naruta, Y.; Satao, K.; Soga, O. Chem. Lett. 1981, 47.
  • 35
  • 36
    • 0025948552 scopus 로고
    • For a review on nucleophilic additions to quinones, see: e
    • For a review on nucleophilic additions to quinones, see: (e) Kutyrev, A. A. Tetrahedron 1991, 47, 8043.
    • (1991) Tetrahedron , vol.47 , pp. 8043
    • Kutyrev, A.A.1
  • 41
    • 36349035246 scopus 로고    scopus 로고
    • 1,2-Naphthoquinones are unusually stable compared with o-benzoquinones and their use as Michael acceptors is better established. For additions of β-dicarbonyl compounds, see: (a) Grinev, A. N.; Arsenichev, I. K.; Nikolaeva I. S.; Golovanova, L. A.; Pushkina, T. V.; Okinskevich, O. V.; Fomina, A. N.; Pershin, G. N. Khim. Farm. Zh. 1985, 19, 699.
    • 1,2-Naphthoquinones are unusually stable compared with o-benzoquinones and their use as Michael acceptors is better established. For additions of β-dicarbonyl compounds, see: (a) Grinev, A. N.; Arsenichev, I. K.; Nikolaeva I. S.; Golovanova, L. A.; Pushkina, T. V.; Okinskevich, O. V.; Fomina, A. N.; Pershin, G. N. Khim. Farm. Zh. 1985, 19, 699.
  • 43
    • 0032821545 scopus 로고    scopus 로고
    • Christoffers, J, Mann, A. Eur. J. Org. Chem. 1999, 2511. For an isolated example of a quinine-catalyzed addition to 1.2-naphthoquinone leading to a 4-substituted-1,2-naphthoquinone, see ref 12
    • (c) Christoffers, J.; Mann, A. Eur. J. Org. Chem. 1999, 2511. For an isolated example of a quinine-catalyzed addition to 1.2-naphthoquinone leading to a 4-substituted-1,2-naphthoquinone, see ref 12.
  • 44
    • 34247232276 scopus 로고    scopus 로고
    • After 24 h, a complex mixture of products was obtained in the case of 3-methoxy- and 3-tert-butylquinones. o-Benzoquinone is known to decompose through dimerization and polymerization pathways; see: Harley-Mason, J.; Laird, A. H. J. Chem. Soc. 1958, 1718.
    • After 24 h, a complex mixture of products was obtained in the case of 3-methoxy- and 3-tert-butylquinones. o-Benzoquinone is known to decompose through dimerization and polymerization pathways; see: Harley-Mason, J.; Laird, A. H. J. Chem. Soc. 1958, 1718.
  • 45
    • 33645455231 scopus 로고    scopus 로고
    • For examples of conjugate additions using cat. 12, see: (a) Wang, Y, Liu, X, Deng, L. J. Am. Chem. Soc. 2006, 128, 3928
    • For examples of conjugate additions using cat. 12, see: (a) Wang, Y.; Liu, X.; Deng, L. J. Am. Chem. Soc. 2006, 128, 3928.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.