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Volumn 46, Issue 21, 2007, Pages 3951-3954

Asymmetric assembly of aromatic rings to produce tetra-ortho-substituted axially chiral biaryl phosphorus compounds

Author keywords

Alkynes; Biaryls; Cycloaddition; Phosphorus; Rhodium

Indexed keywords

CATALYST ACTIVITY; CYCLOADDITION; ENANTIOSELECTIVITY; RHODIUM COMPOUNDS; SUBSTITUTION REACTIONS; TOLUENE;

EID: 34250771917     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200700064     Document Type: Article
Times cited : (157)

References (50)
  • 5
    • 33845278920 scopus 로고    scopus 로고
    • For pioneering work on the enantioselective synthesis of axially chiral biaryl compounds by metal-catalyzed cross-coupling, see: T. Hayashi, K. Hayashizaki, T. Kiyoi, Y. Ito, J. Am. Chem. Soc. 1988, 110, 8153-8154
    • For pioneering work on the enantioselective synthesis of axially chiral biaryl compounds by metal-catalyzed cross-coupling, see: T. Hayashi, K. Hayashizaki, T. Kiyoi, Y. Ito, J. Am. Chem. Soc. 1988, 110, 8153-8154.
  • 6
    • 33746270803 scopus 로고    scopus 로고
    • For recent reviews concerning the atroposelective synthesis of axially chiral biaryl compounds, see: a
    • For recent reviews concerning the atroposelective synthesis of axially chiral biaryl compounds, see: a) G. Bringmann, A. J. P. Mortimer, P. A. Keller, M. J. Gresser, J. Garner, M. Breuning, Angew. Chem. 2005, 117, 5518-5563;
    • (2005) Angew. Chem , vol.117 , pp. 5518-5563
    • Bringmann, G.1    Mortimer, A.J.P.2    Keller, P.A.3    Gresser, M.J.4    Garner, J.5    Breuning, M.6
  • 7
    • 24644462889 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 5384-5427;
    • (2005) Chem. Int. Ed , vol.44 , pp. 5384-5427
    • Angew1
  • 10
    • 33845252502 scopus 로고    scopus 로고
    • For recent reviews of transition-metal-catalyzed [2+2+2] cycloadditions, see: a P. R. Chopade, J. Louie, Adv. Synth. Catal. 2006, 348, 2307-2327;
    • For recent reviews of transition-metal-catalyzed [2+2+2] cycloadditions, see: a) P. R. Chopade, J. Louie, Adv. Synth. Catal. 2006, 348, 2307-2327;
  • 18
    • 0346780615 scopus 로고    scopus 로고
    • For our first report on inter- and intramolecular [2+2+2] cycloadditions catalyzed by a cationic complex between rhodium(I) and a modified binap ligand, see: K. Tanaka, K. Shirasaka, Org. Lett. 2003, 5, 4697-4699.
    • For our first report on inter- and intramolecular [2+2+2] cycloadditions catalyzed by a cationic complex between rhodium(I) and a modified binap ligand, see: K. Tanaka, K. Shirasaka, Org. Lett. 2003, 5, 4697-4699.
  • 19
    • 14544299221 scopus 로고    scopus 로고
    • For the application of cationic rhodium(I)/modified-binap complexes to the synthesis of cyclophanes, see: a) K. Tanaka, K. Toyoda, A. Wada, K. Shirasaka, M. Hirano, Chem. Eur. J. 2005, 11, 1145-1156;
    • For the application of cationic rhodium(I)/modified-binap complexes to the synthesis of cyclophanes, see: a) K. Tanaka, K. Toyoda, A. Wada, K. Shirasaka, M. Hirano, Chem. Eur. J. 2005, 11, 1145-1156;
  • 22
    • 27144521700 scopus 로고    scopus 로고
    • For the application of cationic rhodium(I)/modified-binap complexes to the synthesis of heterocycles, see: a) K. Tanaka, A. Wada, K. Noguchi, Org. Lett. 2005, 7, 4737-4739;
    • For the application of cationic rhodium(I)/modified-binap complexes to the synthesis of heterocycles, see: a) K. Tanaka, A. Wada, K. Noguchi, Org. Lett. 2005, 7, 4737-4739;
  • 25
    • 34250698924 scopus 로고    scopus 로고
    • For the application of cationic rhodium(I)/modified-binap complexes to the synthesis of axially chiral compounds, see: a) K. Tanaka, G. Nishida, A. Wada, K. Noguchi, Angew. Chem. 2004, 116, 6672-6674;
    • For the application of cationic rhodium(I)/modified-binap complexes to the synthesis of axially chiral compounds, see: a) K. Tanaka, G. Nishida, A. Wada, K. Noguchi, Angew. Chem. 2004, 116, 6672-6674;
  • 26
    • 11144315960 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 6510-6512;
    • (2004) Chem. Int. Ed , vol.43 , pp. 6510-6512
    • Angew1
  • 30
    • 33947244017 scopus 로고    scopus 로고
    • K. Tanaka, T. Suda, K. Noguchi, M. Hirano, J. Org. Chem. 2007, 72, 2243-2246; see also Ref. [11a].
    • e) K. Tanaka, T. Suda, K. Noguchi, M. Hirano, J. Org. Chem. 2007, 72, 2243-2246; see also Ref. [11a].
  • 31
    • 0033538606 scopus 로고    scopus 로고
    • For pioneering work on the synthesis of biaryl compounds through alkyne cyclotrimerization, see
    • For pioneering work on the synthesis of biaryl compounds through alkyne cyclotrimerization, see: Y. Sato, K. Ohashi, M. Mori, Tetrahedron Lett. 1999, 40, 5231-5234.
    • (1999) Tetrahedron Lett , vol.40 , pp. 5231-5234
    • Sato, Y.1    Ohashi, K.2    Mori, M.3
  • 32
    • 34250781092 scopus 로고    scopus 로고
    • I catalysis): a) A. Gutnov, B. Heller, C. Fischer, H.-J. Drexler, A. Spannenberg, B. Sundermann, C. Sundermann, Angew. Chem. 2004, 116, 3883-3886;
    • I catalysis): a) A. Gutnov, B. Heller, C. Fischer, H.-J. Drexler, A. Spannenberg, B. Sundermann, C. Sundermann, Angew. Chem. 2004, 116, 3883-3886;
  • 33
    • 4544286694 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 3795-3797;
    • (2004) Chem. Int. Ed , vol.43 , pp. 3795-3797
    • Angew1
  • 34
    • 3142763237 scopus 로고    scopus 로고
    • I catalysis, see: b T. Shibata, T. Fujimoto, K. Yokota, K. Takagi, J. Am. Chem. Soc. 2004, 126, 8382-8383;
    • I catalysis, see: b) T. Shibata, T. Fujimoto, K. Yokota, K. Takagi, J. Am. Chem. Soc. 2004, 126, 8382-8383;
  • 36
    • 34250718621 scopus 로고    scopus 로고
    • For the synthesis of racemic phosphorus-containing biaryl compounds through Diels-Alder reactions with phosphorus-containing dienophiles, see: B. O. Ashburn, R. G. Carter, Angew. Chem. 2006, 118, 1819-1822;
    • For the synthesis of racemic phosphorus-containing biaryl compounds through Diels-Alder reactions with phosphorus-containing dienophiles, see: B. O. Ashburn, R. G. Carter, Angew. Chem. 2006, 118, 1819-1822;
  • 37
    • 33750192986 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 6737-6741.
    • (2006) Chem. Int. Ed , vol.45 , pp. 6737-6741
    • Angew1
  • 38
    • 22544487819 scopus 로고    scopus 로고
    • For highly diastereoselective cobalt-mediated [2+2+2] cyclo-additions of substituted linear enediyne phosphine oxides, see: a M. Schelper, O. Buisine, S. Kozhushkov, C. Aubert, A. de Meijere, M. Malacria, Eur. J. Org. Chem. 2005, 3000-3007;
    • For highly diastereoselective cobalt-mediated [2+2+2] cyclo-additions of substituted linear enediyne phosphine oxides, see: a) M. Schelper, O. Buisine, S. Kozhushkov, C. Aubert, A. de Meijere, M. Malacria, Eur. J. Org. Chem. 2005, 3000-3007;
  • 44
    • 33846585041 scopus 로고    scopus 로고
    • The synthesis of phosphorus-bearing axially chiral biaryl compounds by Co-catalyzed asymmetric cross-cyclotrimerization has been described very recently. However, yields and ee values are not sufficient: a B. Heller, A. Gutnov, C. Fischer, H.-J. Drexler, A. Spannenberg, D. Redkin, C. Sundermann, B. Sundermann, Chem. Eur. J. 2007, 13, 1117-1128;
    • The synthesis of phosphorus-bearing axially chiral biaryl compounds by Co-catalyzed asymmetric cross-cyclotrimerization has been described very recently. However, yields and ee values are not sufficient: a) B. Heller, A. Gutnov, C. Fischer, H.-J. Drexler, A. Spannenberg, D. Redkin, C. Sundermann, B. Sundermann, Chem. Eur. J. 2007, 13, 1117-1128;
  • 45
    • 33750485032 scopus 로고    scopus 로고
    • For the Rh-catalyzed synthesis of amide-substituted chiral biaryls, see: b
    • For the Rh-catalyzed synthesis of amide-substituted chiral biaryls, see: b) M. R. Tracey, J. Oppenheimer, R. P. Hsung, J. Org. Chem. 2006, 71, 8629-8632.
    • (2006) J. Org. Chem , vol.71 , pp. 8629-8632
    • Tracey, M.R.1    Oppenheimer, J.2    Hsung, R.P.3
  • 47
    • 34250702644 scopus 로고    scopus 로고
    • Yin and Buchwald demonstrated that both a phosphonate and a phosphine oxide can be converted readily into phosphines in high yield without racemization; see Ref, 7
    • Yin and Buchwald demonstrated that both a phosphonate and a phosphine oxide can be converted readily into phosphines in high yield without racemization; see Ref. [7].
  • 50
    • 33746283734 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 4321-4326.
    • (2006) Chem. Int. Ed , vol.45 , pp. 4321-4326
    • Angew1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.