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Volumn 73, Issue 15, 2008, Pages 6041-6044

Applications of enantioselective carbolithiation of ortho-substituted β-methylstyrenes

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; ETHERS; NITROGEN COMPOUNDS; ORGANIC COMPOUNDS;

EID: 48149115995     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800941h     Document Type: Article
Times cited : (25)

References (46)
  • 10
    • 0027475137 scopus 로고    scopus 로고
    • Clark, R. D.; Jahangir, Tetrahedron 1993, 49, 1351.
    • (b) Clark, R. D.; Jahangir, Tetrahedron 1993, 49, 1351.
  • 21
    • 0000554392 scopus 로고    scopus 로고
    • Clark, R. D.; Jahangir, J. Org. Chem. 1987, 52, 5378.
    • (d) Clark, R. D.; Jahangir, J. Org. Chem. 1987, 52, 5378.
  • 31
    • 0037427235 scopus 로고    scopus 로고
    • For examples of intermolecular carbolithiation for heterocycle synthesis, see: (a) Coleman, C. M, O'Shea, D. F. J. Am. Chem. Soc. 2003, 125, 4054
    • For examples of intermolecular carbolithiation for heterocycle synthesis, see: (a) Coleman, C. M.; O'Shea, D. F. J. Am. Chem. Soc. 2003, 125, 4054.
  • 38
    • 0030761763 scopus 로고    scopus 로고
    • For enantioselective carbolithiation of β-methylstyrene, see: a
    • For enantioselective carbolithiation of β-methylstyrene, see: (a) Norsikian, S.; Marek, I.; Normant, J. F. Tetrahedron Lett. 1997, 38, 7523.
    • (1997) Tetrahedron Lett , vol.38 , pp. 7523
    • Norsikian, S.1    Marek, I.2    Normant, J.F.3
  • 40
    • 0033623224 scopus 로고    scopus 로고
    • Carbolithiation results in the formation of a chiral benzylic lithium species 6; however, this configurationally unstable chiral center is lost if converted to aromatic heterocycle 8. For examples of resolution of configurationally unstable benzylic lithium centers generated by lateral deprotonation, see: (a) Beak, P.; Anderson, D. R.; Curtis, M. D.; Laumer, J. M.; Pippel, D. J.; Weisenburger, G. A. Acc. Chem. Res. 2000, 33, 715.
    • Carbolithiation results in the formation of a chiral benzylic lithium species 6; however, this configurationally unstable chiral center is lost if converted to aromatic heterocycle 8. For examples of resolution of configurationally unstable benzylic lithium centers generated by lateral deprotonation, see: (a) Beak, P.; Anderson, D. R.; Curtis, M. D.; Laumer, J. M.; Pippel, D. J.; Weisenburger, G. A. Acc. Chem. Res. 2000, 33, 715.
  • 41
    • 0343923544 scopus 로고    scopus 로고
    • For examples by styrene carbolithiation, see: b
    • For examples by styrene carbolithiation, see: (b) Wei, X.; Taylor, R. J. K. Tetrahedron: Asymmetry 1997, 8, 665.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 665
    • Wei, X.1    Taylor, R.J.K.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.