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Volumn 71, Issue 23, 2006, Pages 8748-8754

Divergent chemical synthesis of prolines bearing fluorinated one-carbon units at the 4-position via nucleophilic 5-endo-trig cyclizations

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ETHERS; HYDROGENATION; MOLECULAR DYNAMICS; OXIDATION; SYNTHESIS (CHEMICAL);

EID: 33750861305     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061421n     Document Type: Article
Times cited : (38)

References (55)
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    • (1999) Comprehensive Asymmetric Catalysts I-III
  • 21
    • 0003416163 scopus 로고
    • Kukhar, V. P., Soloshonok, V. A., Eds.; Wiley: Chichester, West Sussex, England
    • (b) Fluorine-Containing Amino Acids, Synthesis and Properties; Kukhar, V. P., Soloshonok, V. A., Eds.; Wiley: Chichester, West Sussex, England, 1995.
    • (1995) Fluorine-Containing Amino Acids, Synthesis and Properties
  • 22
    • 0003518240 scopus 로고    scopus 로고
    • Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; American Chemical Society: Washington, DC
    • Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; American Chemical Society: Washington, DC, 1996.
    • (1996) Biomedical Frontiers of Fluorine Chemistry
  • 25
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    • For a review, see
    • For a review, see: (c) Welch, J. T. Tetrahedron 1987, 43, 3123.
    • (1987) Tetrahedron , vol.43 , pp. 3123
    • Welch, J.T.1
  • 28
    • 0002701930 scopus 로고
    • Trost, B. M., Ed.; Pergamon: Oxford
    • Lee, V. J. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 4, pp 69.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 69
    • Lee, V.J.1
  • 46
    • 33750860862 scopus 로고    scopus 로고
    • note
    • In the Mitsunobu reaction of 4a, the yield of 5a was improved by using toluene instead of THF as a solvent with a decrease in the amount of elimination product, a diene.
  • 47
    • 33750883983 scopus 로고    scopus 로고
    • note
    • The 2,4-anti/syn stereochemistry of the pyrrolidine ring was determined by a NOESY experiment on 2-(4-bromophenyl)-1-(4-methylbenzenesulfonyl)-4- (trifluoromethyl)pyrrolidine (7d) as a representative example. A cross peak between the 2- and 4-protons was not observed in the major product, but in the minor product. As for the 4-proton of the pyrrolidine ring, the signal of the anti-isomer was observed at lower field (δ 2.92) than that of the syn-isomer (δ 2.64), with this spectral criterion confirming similar stereochemistry for 7a-c.
  • 52
    • 33750845687 scopus 로고    scopus 로고
    • note
    • Attempted TEMPO-catalyzed oxidation of 10 with trichloroisocyanuric acid was not successful due to affecting the difluromethylene moiety.
  • 53
    • 0000472668 scopus 로고
    • Removal of the tosyl group on the nitrogen was achieved by photoinduced reduction of the benzyl ester derived from 11 in the presence of 1,5-dimethoxynaphthalene and ascorbic acid. Hamada, T.; Nishida, A.; Yonemitsu, O. J. Am. Chem. Soc. 1986, 108, 140.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 140
    • Hamada, T.1    Nishida, A.2    Yonemitsu, O.3
  • 54
    • 18744403709 scopus 로고    scopus 로고
    • and references therein
    • 13C NMR data proved to be those of a diastereomer mixture. See also: Qiu, X.-L.; Qing, F.-L. J. Org. Chem. 2005, 70, 3826 and references therein.
    • (2005) J. Org. Chem. , vol.70 , pp. 3826
  • 55
    • 33750893764 scopus 로고    scopus 로고
    • note
    • The 2,4-anti/syn stereochemistry of the pyrrolidine ring was determined by a NOESY experiment on TBS protected prolinol 14 as a representative example. Cross peaks between the 2-proton and the 5α-proton and between the 5β-proton and the difluoromethyl proton were observed as shown below.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.