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Volumn , Issue 12, 2001, Pages 1334-1335

An efficient method for the preparation of vicinal tertiary diamines by reductive coupling of aminoacetals mediated by low valent titanium iodide species

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EID: 0035528559     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2001.1334     Document Type: Article
Times cited : (6)

References (18)
  • 2
    • 0001605152 scopus 로고
    • ed. by B. M. Trost and I. Fleming, Pergamon Press, Oxford
    • For reviews, see: a) G. M. Robertson, in "Comprehensive Organic Synthesis," ed. by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 3, p 563.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 563
    • Robertson, G.M.1
  • 5
    • 0001321321 scopus 로고    scopus 로고
    • Recent reports of preparation of vicinal diamines by reductive coupling of aldimines mediated by LVT, see: d) S. Talukdar and A. Banerji, J. Org. Chem., 63, 3468 (1998).
    • (1998) J. Org. Chem. , vol.63 , pp. 3468
    • Talukdar, S.1    Banerji, A.2
  • 14
    • 0007236942 scopus 로고    scopus 로고
    • note
    • Copper powder was used after drying under vacuum at 100 °C. Zinc powder was activated before use with 1 M aqueous hydrochloric acid and washed with water and ether, then dried under vacuum at 100 °C.
  • 15
    • 0007300988 scopus 로고    scopus 로고
    • note
    • 4 (1.11 g, 2.0 mmol) and zinc powder (0.26 g, 4.0 mmol) was added THF (10 mL) under argon atmosphere. The color was changed immediately to dark brown and the mixture was further stirred for 3 h at room temperature. Resulted dark brown supernatant solution (6.5 mL, 1.3 mmol Ti) was added to additional zinc powder (0.170 g, 2.6 mmol) and the mixture was stirred for another 30 min. Resulted dark brown suspension was cooled to O °C and α-(diethylamino)benzyl ethyl ether (0.207 g, 1.0 mmol) was added. The reaction mixture was further stirred for 3 h, and then saturated aqueous sodium hydrogen-carbonate was added. The mixture was filtered and extracted with dichloromethane, and the organic layer was washed with saturated aqueous sodium chloride, dried over sodium sulfate. After filtration and concentration, the crude product was purified by thin layer chromatography to afford the desired vicinal tertiary diamine (dl-isomer 0.070 g, 43% yield, meso-isomer 0.084 g, 52% yield).
  • 16
    • 0007169493 scopus 로고    scopus 로고
    • note
    • 4 using double molar amounts of the respective initial and additional zinc, the yields of diamine decreased (72% yield [ dl / meso = 48 / 52 ] and 69% yield [ dl / meso = 40 / 60 ], respectively).
  • 17
    • 0002267351 scopus 로고    scopus 로고
    • In the case of reductive coupling of aldimine, it was reported that the reaction was effectively promoted by only zinc in aqueous basic media, see: a) M. P. Dutta, B. Baruah, A. Boruah, D. Prajapati, and J. S. Sandhu, Synlett, 1998, 857.
    • Synlett , vol.1998 , pp. 857
    • Dutta, M.P.1    Baruah, B.2    Boruah, A.3    Prajapati, D.4    Sandhu, J.S.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.