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Volumn 70, Issue 18, 2005, Pages 7149-7158

Substitution of hydroxybiaryls via directed ortho-lithiation of N-silylated O-aryl N-isopropylcarbamates

Author keywords

[No Author keywords available]

Indexed keywords

CARBON MONOXIDE; CHEMICAL BONDS; CHEMICAL REACTIONS; ESTERS;

EID: 24144466864     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0506938     Document Type: Article
Times cited : (36)

References (63)
  • 1
    • 0012397313 scopus 로고
    • For reviews, see: (a) Snieckus, V. Chem. Rev. 1990, 90, 879-933.
    • (1990) Chem. Rev. , vol.90 , pp. 879-933
    • Snieckus, V.1
  • 2
    • 0141713788 scopus 로고    scopus 로고
    • Astruc, D., Ed.; Wiley-VCH: Weinheim, Germany
    • (b) Härtung, C. G.; Snieckus, V. In Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: Weinheim, Germany, 2002; pp 330-367.
    • (2002) Modern Arene Chemistry , pp. 330-367
    • Härtung, C.G.1    Snieckus, V.2
  • 3
    • 22244435422 scopus 로고    scopus 로고
    • Rappoport, Z., Marek, I., Eds.; Wiley: Chichester, U.K.
    • (c) Clayden, J. In The Chemistry of Organolithium Compounds; Rappoport, Z., Marek, I., Eds.; Wiley: Chichester, U.K., 2004; pp 495-646.
    • (2004) The Chemistry of Organolithium Compounds , pp. 495-646
    • Clayden, J.1
  • 6
    • 0004219714 scopus 로고    scopus 로고
    • Schlosser, M., Ed.; Wiley: Chichester, U.K.
    • (b) Schlosser, M. In Organometallics in Synthesis, 2nd ed.; Schlosser, M., Ed.; Wiley: Chichester, U.K., 2002; pp 1-352. See also ref 1c.
    • (2002) Organometallics in Synthesis, 2nd Ed. , pp. 1-352
    • Schlosser, M.1
  • 9
    • 0001207373 scopus 로고
    • Side product formation by this rearrangement may be avoided in certain cases by using lower reaction temperatures; for an example, see: (a) Wang, W.; Snieckus, V. J. Org. Chem. 1992, 57, 424-426.
    • (1992) J. Org. Chem. , vol.57 , pp. 424-426
    • Wang, W.1    Snieckus, V.2
  • 17
    • 33645591959 scopus 로고    scopus 로고
    • Unpublished results
    • 2Zr(H)Cl has been developed: Morin, J.; Snieckus, V. Unpublished results.
    • Morin, J.1    Snieckus, V.2
  • 20
    • 84985580904 scopus 로고
    • Direct N,C-dilithiation of O-aryl N-monoalkylcarbamates cannot be achieved due to an irreversible cleavage reaction of the initial formed N-lithiated intermediate (see ref 9). In contrast to this observation, the analogues O-allyl and S-allyl carbamates can be converted to the dianionic species, see: (a) Hanko, R.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1981, 20, 127-128.
    • (1981) Angew. Chem., Int. Ed. Engl. , vol.20 , pp. 127-128
    • Hanko, R.1    Hoppe, D.2
  • 24
    • 0014243185 scopus 로고
    • The N-monoalkylcarbamoyl group has been used as protecting group for phenols of tyrosine derivatives: (b) Jäger, G.; Geiger, R.; Siedel, W. Chem. Ber. 1968, 101, 2762-2770.
    • (1968) Chem. Ber. , vol.101 , pp. 2762-2770
    • Jäger, G.1    Geiger, R.2    Siedel, W.3
  • 28
    • 33645592750 scopus 로고    scopus 로고
    • note
    • Normally, the salt TMEDA-HOTf precipitates as an oil, which solidifies on cooling to -78 °C. Due to its consistency, it undergoes reaction more slowly than 3 with the alkyllithium reagent. As a result, even when applying only 1.1 equiv of butyllithium, high yields of 6 are achieved (see ref 9).
  • 29
    • 33645587074 scopus 로고    scopus 로고
    • note
    • The oxazinone byproduct 10 reacted under deprotection conditions C (see Table 2, entry 3) as well as carbamate 9e to the corresponding salicylic aldehyde 15c, so that a high overall yield was obtained.
  • 30
    • 11244296859 scopus 로고    scopus 로고
    • de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany
    • The purification and analysis of organoboronic acids are generally difficult due to their spontaneous condensation to various degrees to boroxines; for a discussion of possibilities for their derivatization and isolation, see: (a) Miyaura, N. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; pp 41-123.
    • (2004) Metal-Catalyzed Cross-Coupling Reactions, 2nd Ed. , pp. 41-123
    • Miyaura, N.1
  • 31
    • 33645596870 scopus 로고
    • Köster, R., Ed.; Thieme: Stuttgart, Germany
    • See also ref 26c. For a general review on organoboronic acids and their esters, see: (b) Köster, R. In Methoden der Organischen Chemie (Houben-Weyl), 4th ed.; Köster, R., Ed.; Thieme: Stuttgart, Germany, 1982; Vol. 13/3a, pp 489-852.
    • (1982) Methoden der Organischen Chemie (Houben-Weyl), 4th Ed. , vol.13 , Issue.3 A , pp. 489-852
    • Köster, R.1
  • 33
    • 33645585891 scopus 로고    scopus 로고
    • note
    • 3 (94%) and treatment of the resulting phenol with isopropyl isocyanate (95%). The exact procedure will be published elsewhere, see ref 22.
  • 39
    • 2042498074 scopus 로고
    • Hanack, M., Ed.; Thieme: Stuttgart, Germany
    • + synthon, see: (b) Brandsma, L. In Methoden der Organischen Chemie (Houben-Weyl), 4th ed.; Hanack, M., Ed.; Thieme: Stuttgart, Germany, 1993; Vol. E19d, pp 369-447. See also ref 1a.
    • (1993) Methoden der Organischen Chemie (Houben-Weyl), 4th Ed. , vol.E19D , pp. 369-447
    • Brandsma, L.1
  • 41
    • 0000718373 scopus 로고    scopus 로고
    • For reviews of 1,1′-binaphthyl systems, including BINOL derivatives, see: (a) Pu, L. Chem. Rev. 1998, 98, 2405-2494.
    • (1998) Chem. Rev. , vol.98 , pp. 2405-2494
    • Pu, L.1
  • 47
    • 33645600138 scopus 로고    scopus 로고
    • note
    • The complete retention of chirality (≥99% ee) during the BINOL substitution was proved by HPLC analysis of (R)-25 and (R)-28, see Experimental Section.
  • 52
    • 0026458587 scopus 로고
    • (b) Erdik, E. Tetrahedron 1992, 48, 9577-9648.
    • (1992) Tetrahedron , vol.48 , pp. 9577-9648
    • Erdik, E.1
  • 54
    • 14344266665 scopus 로고    scopus 로고
    • de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany
    • (b) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; pp 125-161.
    • (2004) Metal-Catalyzed Cross-Coupling Reactions, 2nd Ed. , pp. 125-161
    • Mitchell, T.N.1
  • 56
    • 4644349037 scopus 로고    scopus 로고
    • de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany
    • For reviews of the Heck reaction, see: (a) Bräse, S.; de Meijere, A. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; pp 217-315.
    • (2004) Metal-Catalyzed Cross-Coupling Reactions, 2nd Ed. , pp. 217-315
    • Bräse, S.1    De Meijere, A.2
  • 58
  • 61
    • 33645603131 scopus 로고    scopus 로고
    • note
    • R = 35.4 min for (R)-25).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.