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Volumn 62, Issue 52, 2006, Pages 12197-12203

Preparation of α-amino ketones, β-amino hydroxylamines using asymmetric aza-Henry reactions of N-p-tolylsulfinylimines with nitroethane

Author keywords

Amines; Asymmetric synthesis; Diastereoselectivity; Imines; Sulfoxides

Indexed keywords

ALDEHYDE; ETHANE; HYDROXYLAMINE; IMINE; KETONE DERIVATIVE; NITRO DERIVATIVE; SODIUM HYDROXIDE;

EID: 33750966348     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.10.021     Document Type: Article
Times cited : (29)

References (48)
  • 7
    • 33750953228 scopus 로고    scopus 로고
    • Enantioselective version using metallic catalyst:
  • 15
    • 33750955401 scopus 로고    scopus 로고
    • Enantioselective organocatalytic reactions:
  • 38
    • 33750964823 scopus 로고    scopus 로고
    • note
    • It is noteworthy that in this case when the reaction was carried out using 0.2 equiv of TBAF, a mixture of the corresponding sulfones was obtained, whereas the use of 1 equiv of TBAF affords all four possible diastereoisomers in 38% overall yield.
  • 39
    • 33750954682 scopus 로고    scopus 로고
    • note
    • Complete X-ray data of compounds 3a and 2f have been deposited at the Cambridge Crystallographic Data Centre as CCDC 298296 and CCDC 298297, respectively.
  • 41
    • 33750953403 scopus 로고    scopus 로고
    • Ketone 8a has been already described in:
  • 44
    • 33750947460 scopus 로고    scopus 로고
    • note
    • ® AD column (hex/i-PrOH=90:10, 1 mL/min, T=25 °C).
  • 45
    • 33750942470 scopus 로고    scopus 로고
    • note
    • α-Amino ketones are valuable building blocks in asymmetric synthesis and are not not easily accesible in enantiomerically pure form. See Ref. 15a and references cited therein.
  • 48
    • 33750088994 scopus 로고    scopus 로고
    • For a recent publication dealing with the difficulties of reduction of nitro groups, see:
    • For a recent publication dealing with the difficulties of reduction of nitro groups, see:. Anderson J.C., and Chapman H.A. Synthesis (2006) 3309
    • (2006) Synthesis , pp. 3309
    • Anderson, J.C.1    Chapman, H.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.