메뉴 건너뛰기




Volumn 129, Issue 29, 2007, Pages 9137-9143

Organo[2-(hydroxymethyl)phenyl]dimethylsilanes as mild and reproducible agents for rhodium-catalyzed 1,4-addition reactions

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL ACCEPTORS; GRAM-SCALE SYNTHESIS; REPRODUCIBLE AGENTS; TETRAORGANOSILICON REAGENTS;

EID: 34547468353     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja071969r     Document Type: Article
Times cited : (114)

References (115)
  • 2
    • 0037243669 scopus 로고    scopus 로고
    • For reviews of rhodium-catalyzed reactions, see: a
    • For reviews of rhodium-catalyzed reactions, see: (a) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169.
    • (2003) Chem. Rev , vol.103 , pp. 169
    • Fagnou, K.1    Lautens, M.2
  • 16
    • 0000796405 scopus 로고    scopus 로고
    • Organotri(alkoxy)silanes: (a) Oi, S.; Honma, Y.; Inoue, Y. Org. Lett. 2002, 4, 667.
    • Organotri(alkoxy)silanes: (a) Oi, S.; Honma, Y.; Inoue, Y. Org. Lett. 2002, 4, 667.
  • 23
    • 0035980292 scopus 로고    scopus 로고
    • Organosilanediols: (h) Mori, A.; Danda, Y.; Fujii, T.; Hirabayashi, K.; Osakada, K. J. Am. Chem. Soc. 2001, 123, 10774.
    • Organosilanediols: (h) Mori, A.; Danda, Y.; Fujii, T.; Hirabayashi, K.; Osakada, K. J. Am. Chem. Soc. 2001, 123, 10774.
  • 24
    • 0035929983 scopus 로고    scopus 로고
    • Organochlorosilanes: (i) Huang, T.-S.; Li, C.-J. Chem. Commun. 2001, 2348.
    • Organochlorosilanes: (i) Huang, T.-S.; Li, C.-J. Chem. Commun. 2001, 2348.
  • 25
    • 0036166723 scopus 로고    scopus 로고
    • Organosilicones: (j) Koike, T.; Du, X.; Mori, A.; Osakada, K. Synlett 2002, 301.
    • Organosilicones: (j) Koike, T.; Du, X.; Mori, A.; Osakada, K. Synlett 2002, 301.
  • 26
    • 0242551501 scopus 로고    scopus 로고
    • For palladium-catalyzed reactions, see: k
    • For palladium-catalyzed reactions, see: (k) Nishikata, T.; Yamamoto, Y.; Miyaura, N. Chem. Lett. 2003, 32, 752.
    • (2003) Chem. Lett , vol.32 , pp. 752
    • Nishikata, T.1    Yamamoto, Y.2    Miyaura, N.3
  • 28
    • 33846896394 scopus 로고    scopus 로고
    • Gini, F.; Hessen, B.; Feringa, B. L.; Minnaard, A. J. Chem. Commun. 2007, 710. See also ref 3d and ref 3f.
    • (m) Gini, F.; Hessen, B.; Feringa, B. L.; Minnaard, A. J. Chem. Commun. 2007, 710. See also ref 3d and ref 3f.
  • 40
    • 4644334182 scopus 로고    scopus 로고
    • For palladium-catalyzed reactions, see: (b) Nishikata, T.; Yamamoto, Y.; Miyaura, N. Chem. Commun. 2004, 1822. See also ref 3f.
    • For palladium-catalyzed reactions, see: (b) Nishikata, T.; Yamamoto, Y.; Miyaura, N. Chem. Commun. 2004, 1822. See also ref 3f.
  • 44
    • 0000487195 scopus 로고
    • Trost, B. M, Fleming, I. Eds. Pergamon Oxford
    • (a) Hiyama, T.; Kusumoto, T. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds. Pergamon Oxford 1991;Vol. 8, pp 763-792.
    • (1991) Comprehensive Organic Synthesis , vol.8 , pp. 763-792
    • Hiyama, T.1    Kusumoto, T.2
  • 68
    • 0026453698 scopus 로고
    • For use of these reagents for allylation of aldehydes, see: e
    • For use of these reagents for allylation of aldehydes, see: (e) Hudrlik, P. F.; Abdallah, Y. M.; Hudrlik, A. M. Tetrahedron Lett. 1992, 33, 6747.
    • (1992) Tetrahedron Lett , vol.33 , pp. 6747
    • Hudrlik, P.F.1    Abdallah, Y.M.2    Hudrlik, A.M.3
  • 70
    • 0344299286 scopus 로고    scopus 로고
    • For the use of tetraorganosilanes as masked silanols, see: a
    • For the use of tetraorganosilanes as masked silanols, see: (a) Denmark, S. E.; Choi, J. Y. J. Am. Chem. Soc. 1999, 121, 5821.
    • (1999) J. Am. Chem. Soc , vol.121 , pp. 5821
    • Denmark, S.E.1    Choi, J.Y.2
  • 76
    • 22744443220 scopus 로고    scopus 로고
    • For a review on kinetic studies using caiorimetry, see
    • For a review on kinetic studies using caiorimetry, see: Blackmond, D. G. Angew. Chem., Int. Ed. 2005, 44, 4302.
    • (2005) Angew. Chem., Int. Ed , vol.44 , pp. 4302
    • Blackmond, D.G.1
  • 78
    • 0000084656 scopus 로고    scopus 로고
    • The isomer would be derived from partial isomerization of (Z)-styrylrhodium intermediate via a plausible rhodium carbene species. For a related isomerization in the rhodium-catalyzed hydrosilylation of alkynes, see: Ojima, I.; Clos, N.; Donovan, R. J.; Ingallina, P. Organometallics 1990, 9, 3127.
    • The isomer would be derived from partial isomerization of (Z)-styrylrhodium intermediate via a plausible rhodium carbene species. For a related isomerization in the rhodium-catalyzed hydrosilylation of alkynes, see: Ojima, I.; Clos, N.; Donovan, R. J.; Ingallina, P. Organometallics 1990, 9, 3127.
  • 80
    • 33748546674 scopus 로고    scopus 로고
    • Recently, Oestreich and coworkers have reported rhodium-catalyzed 1,4-addition reactions of silylboranes, see: (a) Walter, C.; Auer, G.; Oestreich, M. Angew. Chem., Int. Ed. 2006, 45, 5675.
    • Recently, Oestreich and coworkers have reported rhodium-catalyzed 1,4-addition reactions of silylboranes, see: (a) Walter, C.; Auer, G.; Oestreich, M. Angew. Chem., Int. Ed. 2006, 45, 5675.
  • 81
    • 0001374784 scopus 로고
    • For 1,4-addition reactions of disilanes across α,β-unsaturated compounds using palladium or copper catalysts, see: b
    • For 1,4-addition reactions of disilanes across α,β-unsaturated compounds using palladium or copper catalysts, see: (b) Hayashi, T.; Matsumoto, Y.; Ito, Y. Tetrahedron Lett. 1988, 29, 4147.
    • (1988) Tetrahedron Lett , vol.29 , pp. 4147
    • Hayashi, T.1    Matsumoto, Y.2    Ito, Y.3
  • 111
    • 0036845262 scopus 로고    scopus 로고
    • The use of potassium vinylfluoroborate has been reported: (a) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552.
    • The use of potassium vinylfluoroborate has been reported: (a) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552.
  • 114
    • 34547442489 scopus 로고    scopus 로고
    • The absolute configuration has been determined based on the optical rotation compared with that of authentic (S)-1z, α] 20D -52.6 (c 0.98, CHCl3, synthesized from commercially available (S)-2-bromo-α-methylbenzyl alcohol
    • 3), synthesized from commercially available (S)-2-bromo-α-methylbenzyl alcohol.
  • 115
    • 33847312744 scopus 로고    scopus 로고
    • For related mechanism of the transmetalation of arylboronic acids to rhodium(I) via rhodium arylboronate, see: Zhao, P.; Incarvito, C. D.; Hartwig, J. F. J. Am. Chem. Soc. 2007, 129, 1876.
    • For related mechanism of the transmetalation of arylboronic acids to rhodium(I) via rhodium arylboronate, see: Zhao, P.; Incarvito, C. D.; Hartwig, J. F. J. Am. Chem. Soc. 2007, 129, 1876.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.