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Volumn 103, Issue 8, 2003, Pages 3213-3245

Non-symmetrically substituted 1,1′-binaphthyls in enantioselective catalysis

Author keywords

[No Author keywords available]

Indexed keywords

MOLECULAR CRYSTALS; ORGANIC COMPOUNDS; OXIDATION; STOICHIOMETRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); TRANSITION METALS;

EID: 0042880932     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr9900230     Document Type: Article
Times cited : (467)

References (319)
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    • The first axially chiral compound to be prepared in an optically active form was 6,6′-dinitro-2,2′-diphenic acid: Christie, G. H.; Kenner, J. H. J. Chem. Soc. 1922, 614.
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    • 3 (though without knowing the exact structure of the product) was apparently first communicated by Dianin at a Russian meeting in Kazan, as reported by von Richter: von Richter, V. Chem. Ber. 1873, 6, 1252.
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    • Reference 23d gives an 86% yield of 7
    • Reference 23d gives an 86% yield of 7.
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    • note
    • Among the byproducts are the corresponding dibenzocarbazoles (refs 15 and 26).
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    • For definition, see ref 1, pp 316, 364, and 1193
    • For definition, see ref 1, pp 316, 364, and 1193.
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    • note
    • 6,14
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    • note
    • 30
  • 87
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    • note
    • (h) Alternatively, BINOL diacetate can be partly hydrolyzed with 1.5 mM KOH in MeOH (ref 46g).
  • 136
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    • unpublished results. For a DFT study of racemization barriers in 1,1′-binaphthyls, see the following
    • (a) Vyskočil, Š, Kočvský, P., J. Org. Chem. unpublished results. For a DFT study of racemization barriers in 1,1′-binaphthyls, see the following
    • J. Org. Chem.
    • Vyskočil, Š.1    Kočvský, P.2
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    • (b) Toda, F.; Tanaka, K.; Stein, Z.; Goldberg, I. J. Org. Chem. 1994, 59, 5748. The original Toda protocol suffered from a less satisfactory enantioselectivity. A simple switching of the solvent employed for crystallization from methanol to acetonitrile dramatically improved the resolution of BINOL
    • (1994) J. Org. Chem. , vol.59 , pp. 5748
    • Toda, F.1    Tanaka, K.2    Stein, Z.3    Goldberg, I.4
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    • (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046. For electronic effects in related coupling reactions, see
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2046
    • Hartwig, J.F.1
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    • note
    • Note that amination of the free phenol (S) (+)-121 failed, and so its conversion to methyl ether (S)-(+)-119 was indeed necesary.
  • 176
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    • note
    • The efficiency of the resolution is critically dependent on the purity of whose water content has to be minimal.
  • 177
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    • note
    • To be successfully resolved, NOBIN must contain less than 1% of BINAM (3), since this impurity nucleates the crystallization of the opposition enantiomer of the diasteroisomeric salt of 5 and CSA, which substantially lowers the diastereoisomeric purity of the final crop.
  • 220
    • 0038788901 scopus 로고    scopus 로고
    • The related 2-(docyclohexylphosphino)-1-1'-bipphenyl derivative 149e has been shown to undergo an insertion of Pd into the C-H bond in 2'-position, forming a 6-membered palladacycle: (b) Reid, S. M.; Boyle, R. C.; Mague, J. T.; Fink, M. J. J. Am. Chem. Soc. 2003, 125, 7816.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 7816
    • Reid, S.M.1    Boyle, R.C.2    Mague, J.T.3    Fink, M.J.4
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    • For the original reports on the "memory effect" in the Pd(0)-catalyzed allylic substitution, see: (a) Fiaud, J. C.; Malleron, J. L. Tetrahedron Lett. 1981, 22, 1399.
    • (1981) Tetrahedron Lett. , vol.22 , pp. 1399
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    • note
    • The original X-ray structures reported by Hayashi were those for (R)-enantiomers. Chart 9 shows (S)-enantiomers for 204 and 205 in order to allow a clear and direct comparison to be made with our structures of MOP complex 206 and the MAP complexes, which were all (S)-configured (section III.D).
  • 290
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    • note; 199-ANYL
    • The first papers by the two groups were published simultaneously and independently (refs 16, 108, and 120). Note that the two groups first revealed their results at the same ACS symposium in 1998: (a) Buchwald, S. L. Abstr. Pap. Am. Chem. Soc. 1998, 216, 199-ANYL.
    • (1998) Abstr. Pap. Am. Chem. Soc. , vol.216
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    • Note, however, that seven-membered chelates are favored by BINAP
    • (b) Zhang, L.; Zetterberg, K. Organometallics 1991, 10, 3806. Note, however, that seven-membered chelates are favored by BINAP.
    • (1991) Organometallics , vol.10 , pp. 3806
    • Zhang, L.1    Zetterberg, K.2
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    • note
    • 3-intermediate.
  • 307
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    • For the most recent study, using QUINAP as ligand in the rhodium-catalyzed bishydroboration of olefins with bis(catecholatodiboron), producing vicinal syn-doils (≤98% ee), see the following: (b) Morgan, J. B.; Miller, S. P.; Morken, J. P. J. Am. Chem. Soc. 2003, 125, 8702.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 8702
    • Morgan, J.B.1    Miller, S.P.2    Morken, J.P.3
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    • note
    • 4 and quinine [48% ee for PhCOMe and 75% ee for (mesityl)COMe] by Červinka as early as in 1959, i.e., two decades before Noyori: (a) Cervinka O. Chimia 1959, 13, 332.
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    • note
    • Note that NOBIN (5) is now commercially available.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.