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Volumn , Issue 7, 2000, Pages 838-839

Diastereoselective pinacol coupling reaction of aliphatic and aromatic aldehydes promoted by low valent titanium iodide in situ formed by titanium(IV) iodide and copper

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EID: 0034339646     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2000.838     Document Type: Article
Times cited : (16)

References (17)
  • 1
    • 0001605152 scopus 로고
    • ed. by B. M. Trost and I. Fleming, Pergamon Press, Oxford
    • For a review, 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
  • 11
    • 0001607109 scopus 로고    scopus 로고
    • Postulated low valent titanium iodide mediated reducting coupling of carbonyl compounds affording the corresponding olefins was reported by S. Talukdar, S. K. Nayak, and A. Banerji, J. Org. Chem., 63, 4925 (1998).
    • (1998) J. Org. Chem. , vol.63 , pp. 4925
    • Talukdar, S.1    Nayak, S.K.2    Banerji, A.3
  • 12
    • 0001977954 scopus 로고    scopus 로고
    • note
    • Copper powder was purchased from Soekawa Chemical Co., Ltd. and used as received. Other metals were dried under vacuum at 100 °C.
  • 13
    • 0002122807 scopus 로고    scopus 로고
    • note
    • 2 suspended dark brown solution was cooled to 0 °C and a solution of 3-phenylpropionaldehyde (0.5 mmol) in dichloromethane (1.5 ml) was added. The reaction mixture was stirred for 6 hours, and then the work up was done as shown in Ref. 3. The crude product was purified by TLC to afford the desired pinacol and co-product (80% and 11%, respectively).


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