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Volumn 8, Issue 15, 2006, Pages 3371-3374

Aminolysis of resin-bound N-nosylaziridine-2-carboxylic acids

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; AZIRIDINE DERIVATIVE; CARBOXYLIC ACID; HETEROCYCLIC COMPOUND;

EID: 33746932081     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061304e     Document Type: Article
Times cited : (23)

References (46)
  • 12
    • 0030790051 scopus 로고    scopus 로고
    • Previously, nitrobenzenesulfonyl-activated aziridines have been successfully ring opened with amine nucleophiles in solution. See: (a) Maligres, P. E.; See, M. M.; Askin, D.; Reider, P. J. Tetrahedron Lett. 1997, 38, 5253-5256.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 5253-5256
    • Maligres, P.E.1    See, M.M.2    Askin, D.3    Reider, P.J.4
  • 16
    • 1542375289 scopus 로고    scopus 로고
    • (b) Hu, E. X. Tetrahedron 2004, 60, 2701-2742.
    • (2004) Tetrahedron , vol.60 , pp. 2701-2742
    • Hu, E.X.1
  • 18
    • 0028816280 scopus 로고
    • (b) A similar regioselectivity was also described with unprotected acids: Churn, N. J.; Young, D. W. Tetrahedron Lett. 1995, 36, 151-154.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 151-154
    • Churn, N.J.1    Young, D.W.2
  • 19
    • 33746915346 scopus 로고    scopus 로고
    • note
    • 1H NMR data and the RP-HPLC traces suggested equally high conversions/ yields in all six cases.
  • 22
    • 33746891733 scopus 로고    scopus 로고
    • For previous examples of intramolecular Fukuyama-Mitsunobu reactions on solid phase, see: (a) Kung, P. P.; Swayze, E. Tetrahedron Lett. 1999, 40, 6551-5654.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 6551-15654
    • Kung, P.P.1    Swayze, E.2
  • 26
    • 33746911810 scopus 로고    scopus 로고
    • note
    • 3P, 40%.
  • 33
    • 33746896430 scopus 로고    scopus 로고
    • note
    • R (A-3) = 14.4 min.
  • 34
    • 33746872788 scopus 로고    scopus 로고
    • note
    • D +45.2° (c 1.4, MeOH).
  • 35
    • 33746876204 scopus 로고    scopus 로고
    • note
    • 2 and MeOH) were pooled, and the solvents were removed in vacuo. The crude material was dissolved in MeCN (1 mL) and purified by preparative RP-HPLC (17 mg, 33%).
  • 36
    • 27644470502 scopus 로고    scopus 로고
    • For a comprehensive review of previously available methods for formation of the amino functionality of solid phase, see: Olsen, C. A.; Franzyk, H.; Jaroszewski, J. W. Synthesis 2005, 2631-2653.
    • (2005) Synthesis , pp. 2631-2653
    • Olsen, C.A.1    Franzyk, H.2    Jaroszewski, J.W.3
  • 42
    • 33644839988 scopus 로고    scopus 로고
    • For reviews, see: (a) Tan, D. S. Nat. Chem. Biol. 2005, 1, 74-84.
    • (2005) Nat. Chem. Biol. , vol.1 , pp. 74-84
    • Tan, D.S.1
  • 45
    • 0034678033 scopus 로고    scopus 로고
    • (d) Schreiber, S. L. Science 2000, 287, 1964-1969.
    • (2000) Science , vol.287 , pp. 1964-1969
    • Schreiber, S.L.1
  • 46
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    • and references therein
    • For recent examples of aziridination in solution, see: Kim, S. K.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2004, 43, 3952-3954, and references therein.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 3952-3954
    • Kim, S.K.1    Jacobsen, E.N.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.