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Volumn 65, Issue 46, 2009, Pages 9569-9574

Stereoselective synthesis of vicinal diols by the stannous chloride-mediated reaction of unprotected hydroxyallylic stannane with carbonyl compounds

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ARABINOSE; CARBONYL DERIVATIVE; GLYCERALDEHYDE; STANNOUS CHLORIDE; TIN;

EID: 70349728471     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.09.063     Document Type: Article
Times cited : (8)

References (35)
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    • Trost B.M. (Ed), Pergamon, Oxford, UK
    • In: Trost B.M. (Ed). Comprehensive Organic Synthesis Vol. 3 (1991), Pergamon, Oxford, UK 563-611
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 563-611
  • 7
    • 4243973410 scopus 로고
    • and references cited therein
    • McMurry J.E. Chem. Rev. 89 (1989) 1513-1524 and references cited therein
    • (1989) Chem. Rev. , vol.89 , pp. 1513-1524
    • McMurry, J.E.1
  • 10
    • 0001465319 scopus 로고
    • Trost B.M. (Ed), Pergamon, Oxford, UK
    • In: Trost B.M. (Ed). Comprehensive Organic Synthesis Vol. 7 (1991), Pergamon, Oxford, UK 437-448
    • (1991) Comprehensive Organic Synthesis , vol.7 , pp. 437-448
  • 17
    • 45249085012 scopus 로고    scopus 로고
    • Recently, Denmark reported the aldol-type raction using alkoxy-substituted silylketene acetals for synthesis of 1,2-diol derivatives
    • Recently, Denmark reported the aldol-type raction using alkoxy-substituted silylketene acetals for synthesis of 1,2-diol derivatives. Denmark S.E., and Chung W.-j. J. Org. Chem. 73 (2008) 4582-4595
    • (2008) J. Org. Chem. , vol.73 , pp. 4582-4595
    • Denmark, S.E.1    Chung, W.-j.2
  • 21
    • 70349745359 scopus 로고    scopus 로고
    • note
    • 1H NMR using an internal standard before employing the reaction with aldehydes. Preparation of α-hydroxyallylic stannanes and general procedure for the synthesis of vicinal diols are described in Supplementary data.
  • 22
    • 70349743893 scopus 로고    scopus 로고
    • note
    • When using 1c, propionitrile with large amount gave slightly higher yield than acetonitrile in the case of using 1a and 1b.
  • 30
    • 70349753099 scopus 로고    scopus 로고
    • note
    • 3SnCl was confirmed as observable signals. No signals corresponding to the olefinic moiety were confirmed. Therefore, the signals originating from the allylic moiety would be broadened probably because of decomposition by polymerization and/or formation of a complicated mixture.
  • 33
    • 0001510414 scopus 로고
    • A multi-step procedure for transformation from 10 to the d-arabinose derivative was reported
    • A multi-step procedure for transformation from 10 to the d-arabinose derivative was reported. Lee A.W.M., Martin V.S., Masamune S., Sharpless K.B., and Walker F.J. J. Am. Chem. Soc. 104 (1982) 3515-3516
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 3515-3516
    • Lee, A.W.M.1    Martin, V.S.2    Masamune, S.3    Sharpless, K.B.4    Walker, F.J.5
  • 34
    • 70349750118 scopus 로고    scopus 로고
    • note
    • CCDC 737724 (3aa′), 737,725 (3af′), 737,726 (3ag′), 737,727 (3ah′), 737,728 (3cb′), 737,729 (3ck′), 737,730 (3cl), 737,731 (3dl′), 737,732 (7aa′), 737,733 (7ab′), 737,734 (7ad′), and 737,735 (11′) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.