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Volumn 65, Issue 40, 2009, Pages 8362-8366

Highly stereoselective epoxidation of O-protected 3-hydroxy-1-nitroalkenes

Author keywords

Epoxidation; Nitroaldols; Nitrocompounds

Indexed keywords

3 HYDROXY 1 NITROALKENE DERIVATIVE; ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; LACTALDEHYDE; LITHIUM DERIVATIVE; LITHIUM TERT BUTYLPEROXIDE; MANDELALDEHYDE; NUCLEOPHILE; PEROXIDE; POTASSIUM DERIVATIVE; POTASSIUM TERT BUTYLPEROXIDE; UNCLASSIFIED DRUG;

EID: 69249245379     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.08.010     Document Type: Article
Times cited : (12)

References (33)
  • 18
    • 69249205227 scopus 로고    scopus 로고
    • note
    • The epoxidation over the non-protected 3-hydroxy-1-nitroalkenes readily prepared through deprotection of compounds 1 and 4 did not furnish the expected nitroepoxides but a complex mixture of non-epoxidic compounds.
  • 21
    • 69249221118 scopus 로고    scopus 로고
    • For the conversion of nitroepoxides into oximes, see
    • For the conversion of nitroepoxides into oximes, see:
  • 24
    • 69249213254 scopus 로고    scopus 로고
    • note
    • The hydrogenation reaction of nitroepoxide 8 using hydrogen resulted in decomposition.
  • 26
    • 69249210743 scopus 로고    scopus 로고
    • note
    • 2,3 (anti)=6.5 Hz. Similar coupling constants were observed for syn and anti isomers of 1-substituted 3-hydroxy-1-nitroepoxides (Ref. 2d).
  • 29
    • 69249202110 scopus 로고    scopus 로고
    • note
    • The reversibility experiment was also carried out in the presence of nitroalkene 1, also nitroepoxide 8 was obtained and nitroalkene was recovered. Only trans-nitroepoxide are observed as it is from the epoxidation reactions.
  • 30
    • 69249218748 scopus 로고    scopus 로고
    • For conjugate addition of amides to non-substituted and α-methyl-substituted γ-methoxyenoates, see
    • For conjugate addition of amides to non-substituted and α-methyl-substituted γ-methoxyenoates, see:
  • 33
    • 0000471716 scopus 로고
    • Preparation of tert-butyl hydroperoxide solution:
    • Preparation of tert-butyl hydroperoxide solution:. Hill J.G., Rossiter B.E., and Sharpless B. J. Org. Chem. 48 (1983) 3607-3608
    • (1983) J. Org. Chem. , vol.48 , pp. 3607-3608
    • Hill, J.G.1    Rossiter, B.E.2    Sharpless, B.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.