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Volumn 46, Issue 3, 2005, Pages 447-450

α-Hydroxylation of carbonyls using iodine

Author keywords

Hydroxylation; Acyloins; Iodine

Indexed keywords

ALDEHYDE; CARBONYL DERIVATIVE; IODINE; KETONE; METHANOL DERIVATIVE;

EID: 11144286002     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.11.092     Document Type: Article
Times cited : (26)

References (44)
  • 4
    • 0001213599 scopus 로고    scopus 로고
    • For an excellent review concerning the diastereo-selective synthesis of 1,2-diols from nucleophilic addition to α-hydroxyketone derivatives, see: A. Mengel, and O. Reiser Chem. Rev. 99 1999 1191 1223
    • (1999) Chem. Rev. , vol.99 , pp. 1191-1223
    • Mengel, A.1    Reiser, O.2
  • 17
    • 0842343649 scopus 로고    scopus 로고
    • Aldehyde α-hydroxylation: G. Zhong Angew. Chem. 115 2003 4379 4382
    • (2003) Angew. Chem. , vol.115 , pp. 4379-4382
    • Zhong, G.1
  • 24
    • 4243057730 scopus 로고    scopus 로고
    • Angew. Chem., Int. Ed. 43 2004 1112 1115 The initially formed adducts can be converted to the corresponding α-hydroxy carbonyl
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 1112-1115
  • 35
    • 11144316860 scopus 로고
    • Hypervalent iodine reagents iodosobenzene and O-iodosobenzoic acid carry explosion hazards. For example, See V. Gert Chem. Eng. News 30 1989 2
    • (1989) Chem. Eng. News , vol.30 , pp. 2
    • Gert, V.1
  • 37
    • 11144261821 scopus 로고    scopus 로고
    • note
    • 5N: C, 55.16; H, 8.87; N, 5.36. Found: C, 55.14; H, 9.01; N, 5.31. For characterization of 1: Ref. 2a For characterization of 2, 6 and 7 see Ref. 10e and citations therein
  • 38
    • 11144333649 scopus 로고    scopus 로고
    • note
    • 1H NMR). A similar product distribution was observed in Refs. a and b
  • 39
    • 0000266497 scopus 로고
    • Subjection of methyl cyclohexanecarboxylate to the reaction conditions did not result in the formation of 9 but instead returned unreacted ester. For further discussion see Refs. a and b. For related reactions see: B.D. Mookherjee, R.W. Trenkle, and R. Patel J. Org. Chem. 36 1971 3266 3270
    • (1971) J. Org. Chem. , vol.36 , pp. 3266-3270
    • Mookherjee, B.D.1    Trenkle, R.W.2    Patel, R.3
  • 41
    • 0030829196 scopus 로고    scopus 로고
    • 2O: C, 55.50; H, 9.20; N, 4.98. Found C, 55.71; H, 8.95; N, 4.92. For characterization of 11, see Ref. 2a. For characterization of 12, see: H. Yamamoto, M. Tsuda, S. Sakaguchi, and Y. Ishii J. Org. Chem. 62 1997 7174 7177
    • (1997) J. Org. Chem. , vol.62 , pp. 7174-7177
    • Yamamoto, H.1    Tsuda, M.2    Sakaguchi, S.3    Ishii, Y.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.