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Volumn 8, Issue 8, 2006, Pages 1521-1524

Unexpected ring-opening reactions of aziridines with aldehydes catalyzed by nucleophilic carbenes under aerobic conditions

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AZIRIDINE DERIVATIVE; CARBENE; DRUG DERIVATIVE; HYDROCARBON; METHANE;

EID: 33646458516     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0529905     Document Type: Article
Times cited : (98)

References (61)
  • 2
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    • For recent reviews on umpolung reactions involving cyanide or nucleophilic carbene, see: (a) Johnson, J. S. Angew. Chem., Int. Ed. 2004, 43, 1326.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 1326
    • Johnson, J.S.1
  • 21
    • 33646442292 scopus 로고    scopus 로고
    • For comprehensive reviews, see refs 2c and 2e
    • For comprehensive reviews, see refs 2c and 2e.
  • 38
    • 1542375289 scopus 로고    scopus 로고
    • For an excellent review on ring opening of aziridines, see: Hu, X. E. Tetrahedron 2004, 60, 2701.
    • (2004) Tetrahedron , vol.60 , pp. 2701
    • Hu, X.E.1
  • 40
    • 33646450367 scopus 로고    scopus 로고
    • Eds.: Houk, K. N., List, B.
    • (b) Acc. Chem. Res. 2004, 37 (8), special issue (Eds.: Houk, K. N., List, B.).
    • (2004) Acc. Chem. Res. , vol.37 , Issue.8 SPEC. ISSUE
  • 43
    • 33646448223 scopus 로고    scopus 로고
    • note
    • For a review on ring opening of aziridines with carboxylic acid to give a carboxylate of 1,2-amino alcohols, see ref 8.
  • 44
    • 0037201534 scopus 로고    scopus 로고
    • For reviews on β-amino ketones, see: (a) Liu, M.; Sibi, M. P. Tetrahedron 2002, 58, 7991.
    • (2002) Tetrahedron , vol.58 , pp. 7991
    • Liu, M.1    Sibi, M.P.2
  • 47
    • 33646449598 scopus 로고    scopus 로고
    • note
    • Slightly better regioselectivity was obtained in the ring-opening reaction of aziridine 2b and 3a in comparison with what was received with 1d (4.1:1).
  • 52
    • 17444420326 scopus 로고    scopus 로고
    • For the oxidation of aldehydes to thioesters in the presence of a thiazolium salt and azobenzene, see: (b) Kageyama, Y.; Murata, S. J. Org. Chem. 2005, 70, 3140.
    • (2005) J. Org. Chem. , vol.70 , pp. 3140
    • Kageyama, Y.1    Murata, S.2
  • 53
    • 33646452848 scopus 로고    scopus 로고
    • note
    • The phenomena have also been observed recently in the MCR reactions by Nair et al.; see ref 7f.
  • 54
    • 0001424578 scopus 로고
    • For a similar compound related to cyanide showing high nucleophilic activity, see: Stork, G. J. Am. Chem. Soc. 1974, 96, 5272.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 5272
    • Stork, G.1
  • 57
    • 0034669659 scopus 로고    scopus 로고
    • For the reaction of the spin-paired urate and molecular oxygen, see: (c) Sarma, A. D.; Tipton, P. A. J. Am. Chem. Soc. 2000, 122, 11252.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 11252
    • Sarma, A.D.1    Tipton, P.A.2
  • 58
    • 33646445830 scopus 로고    scopus 로고
    • note
    • This catalytic cycle might not account for the ring opening of aziridines by α,β-unsaturated aldehydes. The intramolecular redox of α,β-unsaturated aldehydes promoted by carbene to give the saturated carboxylic acid, and subsequently ring opening of the aziridines, should not be ruled out. See ref 7k-o.
  • 59
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    • and references therein
    • For limited examples of metal-catalyzed enantioselective desymmetrization of meso-aziridines, see: (a) Mita, T.; Fujimori, I.; Wada, R.; Wen, J.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 11252 and references therein.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 11252
    • Mita, T.1    Fujimori, I.2    Wada, R.3    Wen, J.4    Kanai, M.5    Shibasaki, M.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.