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Volumn 14, Issue 14, 2012, Pages 3676-3679

Chlorination of aliphatic primary alcohols via triphosgene-triethylamine activation

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EID: 84864148507     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301520d     Document Type: Article
Times cited : (43)

References (27)
  • 22
    • 84864132796 scopus 로고    scopus 로고
    • CCDC 879959 (compound 2b) and 879960 (compound 2c) contain the supplementary crystallographic data for this paper, which can be obtained free of charge via, or by emailing data-request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, U.K. fax: +44 1223 336033. See SI
    • CCDC 879959 (compound 2b) and 879960 (compound 2c) contain the supplementary crystallographic data for this paper, which can be obtained free of charge via www.ccdc.cam.ac.uk/ data-request/cif, or by emailing data-request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, U.K.; fax: +44 1223 336033. See SI.
  • 26
    • 84864119017 scopus 로고    scopus 로고
    • Ajaykumar, A. S.; Puranik, V. G.; Deshmukh, A. R. A. S. Synthesis 2007, 8, 1159-1164. Deshmukh and co-workers attempted similar triphosgene-TEA chlorination in THF at -20°C using α-branched a diaminoalcohol as a crude dihydrochloride salt (en route to their formal synthesis of (+)-biotin) to give the corresponding chloride in modest yield. Interestingly, when pure 6c was treated under these conditions, the reaction predominantly produced diethylcarbamate 7c and the chlorination product was not observed. We hypothesized that perhaps the rate of chloride substitution in Deshmukh's chemistry was tremendously amplified by the excess residual chloride ions obtained upon evaporation of the 20% HCl/MeOH deprotection solution which was employed to remove the N -Boc precursor
    • (2007) Synthesis , vol.8 , pp. 1159-1164
    • Ajaykumar, A.S.1    Puranik, V.G.2    Deshmukh, A.R.A.S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.