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Volumn 8, Issue 10, 2006, Pages 2183-2186

Aziridinium from N,N-dibenzyl serine methyl ester: Synthesis of enantiomerically pure β-amino and α,β-diamino esters

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; DRUG DERIVATIVE; ESTER; N,N DIBENZYL AZIRIDINIUM 2 CARBOXYLATE; N,N-DIBENZYL AZIRIDINIUM-2-CARBOXYLATE; PROPIONIC ACID DERIVATIVE; SERINE; SERINE METHYL ESTER;

EID: 33744725551     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060700u     Document Type: Article
Times cited : (44)

References (67)
  • 29
    • 0033800394 scopus 로고    scopus 로고
    • For recent reviews on the aziridine chemistry, see: (f) McCoull, W.; Davis, F. A. Synthesis 2000, 10, 1347-1365.
    • (2000) Synthesis , vol.10 , pp. 1347-1365
    • McCoull, W.1    Davis, F.A.2
  • 30
    • 1542375289 scopus 로고    scopus 로고
    • (g) Hu, X. E. Tetrahedron 2004, 60, 2701-2743.
    • (2004) Tetrahedron , vol.60 , pp. 2701-2743
    • Hu, X.E.1
  • 33
  • 41
    • 0031757775 scopus 로고    scopus 로고
    • Certain mesylates derived from N,N-dibenzyl amino alcohol can be purified by low-temperature flash chromatography, see: Thomas, C.; Orecher, F.: Gmeiner, P. Synthesis 1998, 1491-1496.
    • (1998) Synthesis , pp. 1491-1496
    • Thomas, C.1    Orecher, F.2    Gmeiner, P.3
  • 57
    • 0043076447 scopus 로고    scopus 로고
    • For interesting examples of ring opening of aziridine by a vicinal tertiary amine leading to aziridinium, see: (a) Concellón, J. M.; Riego, E. J. Org. Chem. 2003, 68, 6407-6410.
    • (2003) J. Org. Chem. , vol.68 , pp. 6407-6410
    • Concellón, J.M.1    Riego, E.2
  • 60
    • 33845555711 scopus 로고
    • Compound 6 has been converted to the corresponding α-fluoro and α-bromo derivatives via an aziridinium intermediate, see: (a) Somekh, L.; Shanzer, A. J. Am. Chem. Soc. 1982, 104, 5836-5837.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 5836-5837
    • Somekh, L.1    Shanzer, A.2
  • 65
    • 26444568120 scopus 로고    scopus 로고
    • and references therein
    • Mossé, S.; Alexakis, A. Org. Lett. 2005, 7, 4361-4364 and references therein.
    • (2005) Org. Lett. , vol.7 , pp. 4361-4364
    • Mossé, S.1    Alexakis, A.2
  • 66
    • 0034710468 scopus 로고    scopus 로고
    • and references therein
    • Wei, L.; Lubell, W. D. Org. Lett. 2000, 2, 2595-2598 and references therein.
    • (2000) Org. Lett. , vol.2 , pp. 2595-2598
    • Wei, L.1    Lubell, W.D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.