메뉴 건너뛰기




Volumn 50, Issue 47, 2009, Pages 6580-6583

Lewis acid-catalyzed intramolecular amination via 1,3-chirality transfer

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALLYL ALCOHOL; BENZENE; LEWIS ACID; SOLVENT; TETRAHYDROISOQUINOLINE;

EID: 78349237155     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.09.053     Document Type: Article
Times cited : (34)

References (43)
  • 6
    • 0026418434 scopus 로고
    • Trost, B. M. Science 1991, 254, 1471-1477.
    • (1991) Science , vol.254 , pp. 1471-1477
    • Trost, B.M.1
  • 7
    • 4243987144 scopus 로고    scopus 로고
    • For a review of allylic amination
    • For a review of allylic amination: (a) Johannsen, M.; Jørgensen, K. A. Chem. Rev. 1998, 98, 1689-1708;
    • (1998) Chem. Rev. , vol.98 , pp. 1689-1708
    • Johannsen, M.1    Jørgensen, K.A.2
  • 8
    • 16244407390 scopus 로고    scopus 로고
    • For a recent review of palladium-catalyzed C-N bond formation from alcohol
    • For a recent review of palladium-catalyzed C-N bond formation from alcohol: (b) Muzart, J. Tetrahedron 2005, 61, 4179-4212;
    • (2005) Tetrahedron , vol.61 , pp. 4179-4212
    • Muzart, J.1
  • 9
    • 22144461766 scopus 로고    scopus 로고
    • A review of the palladium-catalyzed activation of allylic alcohols
    • A review of the palladium-catalyzed activation of allylic alcohols: (c) Tamaru, Y. Eur. J. Org. Chem. 2005, 2647-2656;
    • (2005) Eur. J. Org. Chem. , pp. 2647-2656
    • Tamaru, Y.1
  • 10
    • 66149171361 scopus 로고    scopus 로고
    • Recent examples of the palladium-catalyzed activation of allylic alcohols
    • Recent examples of the palladium-catalyzed activation of allylic alcohols: (d) Nishikata, T.; Lipshutz, B. H. Org. Lett. 2009, 11, 2377-2379;
    • (2009) Org. Lett. , vol.11 , pp. 2377-2379
    • Nishikata, T.1    Lipshutz, B.H.2
  • 13
    • 2942609168 scopus 로고    scopus 로고
    • Review of Pd(II)-catalyzed reaction
    • Review of Pd(II)-catalyzed reaction: (g) Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285-2309;
    • (2004) Chem. Rev. , vol.104 , pp. 2285-2309
    • Zeni, G.1    Larock, R.C.2
  • 15
    • 40849107812 scopus 로고    scopus 로고
    • For other recent examples of direct substitution of allylic alcohol with amine or amide. Iodine as a catalyst
    • For other recent examples of direct substitution of allylic alcohol with amine or amide. Iodine as a catalyst: (a) Wu, W.; Rao, W.; Er, Y. Q.; Loh, K.; Poh, C. Y.; Chan, P. W. H. Tetrahedron Lett. 2008, 49, 2620-2624;
    • (2008) Tetrahedron Lett. , vol.49 , pp. 2620-2624
    • Wu, W.1    Rao, W.2    Er, Y.Q.3    Loh, K.4    Poh, C.Y.5    Chan, P.W.H.6
  • 32
    • 85031256611 scopus 로고    scopus 로고
    • note
    • 2O followed by deprotection of the silyl group by TBAF in THF giving the alcohol 1 in 75% yield in two steps
  • 37
    • 85031250154 scopus 로고    scopus 로고
    • The enantiomeric ratio was determined by HPLC analysis using daicel chiralcel AD-H. Eluent, hexane/2-propanol (9/1), flow rate: 0.5 mL/min, detection: 254 nm, retention time: 8.1 min (R-isomer), 9.6 min (S-isomer)
    • The enantiomeric ratio was determined by HPLC analysis using daicel chiralcel AD-H. Eluent, hexane/2-propanol (9/1), flow rate: 0.5 mL/min, detection: 254 nm, retention time: 8.1 min (R-isomer), 9.6 min (S-isomer).
  • 40
    • 0034679098 scopus 로고    scopus 로고
    • σ-π Chelation of typical metals was reported by Yamamoto et al.; see
    • σ-π Chelation of typical metals was reported by Yamamoto et al.; see: (b) Asao, N.; Asano, T.; Ohishi, T.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 4817-4818;
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 4817-4818
    • Asao, N.1    Asano, T.2    Ohishi, T.3    Yamamoto, Y.4
  • 42
    • 85031276263 scopus 로고    scopus 로고
    • note
    • 3) δ 1.49 (9H, s), 1.68 (3H, d, J = 6.0 Hz), 2.68-2.76 (1H, m), 2.85-2.96 (1H, m), 3.20 (1H, br s), 4.10 (1H, br s), 5.45-5.64 (3H, m), 7.10-7.21 (4H, m).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.