메뉴 건너뛰기




Volumn 11, Issue 4, 2009, Pages 919-921

Asymmetric Lewis acid mediated [1,2]-rearrangement of proline-derived ammonium ylides

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; PROLINE;

EID: 62749167066     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8028803     Document Type: Article
Times cited : (30)

References (34)
  • 2
    • 33745502124 scopus 로고
    • For reviews on peptidomimetic chemistry, see: a
    • For reviews on peptidomimetic chemistry, see: (a) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244.
    • (1993) Angew. Chem., Int. Ed. Engl , vol.32 , pp. 1244
    • Giannis, A.1    Kolter, T.2
  • 9
    • 55049138759 scopus 로고    scopus 로고
    • Dalko, P. I, Ed, Wiley-VCH: Weinheim
    • Enantioselective Organocatalysis; Dalko, P. I., Ed.; Wiley-VCH: Weinheim, 2007.
    • (2007) Enantioselective Organocatalysis
  • 12
    • 34250023769 scopus 로고    scopus 로고
    • For an example of ester-enolate Claisen rearrangement in synthesis of quaternary prolines, see: a
    • For an example of ester-enolate Claisen rearrangement in synthesis of quaternary prolines, see: (a) Sakaguchi, K.; Yamamoto, M.; Watanabe, Y.; Ohfune, Y. Tetrahedron Lett. 2007, 48, 4821-4824.
    • (2007) Tetrahedron Lett , vol.48 , pp. 4821-4824
    • Sakaguchi, K.1    Yamamoto, M.2    Watanabe, Y.3    Ohfune, Y.4
  • 14
    • 29744470611 scopus 로고    scopus 로고
    • For reviews on Stevens rearrangement, see: a
    • For reviews on Stevens rearrangement, see: (a) Vanecko, J. A.; Wan, H.; West, F. G. Tetrahedron 2006, 62, 1043-1062.
    • (2006) Tetrahedron , vol.62 , pp. 1043-1062
    • Vanecko, J.A.1    Wan, H.2    West, F.G.3
  • 17
    • 0000033512 scopus 로고
    • Trost, B. M, Fleming, I, Eds, Pergamon: Oxford
    • (d) Markó, I. E. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, pp 913-973.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 913-973
    • Markó, I.E.1
  • 21
    • 0029907051 scopus 로고    scopus 로고
    • For the chirality transfer via a chiral borane-amine adduct in alkylation of (S) -N-benzylproline methyl ester, see: Ferey, V.; Vedrenne, P.; Toupet, L.; Le Gall, T.; Mioskowski, C. J. Org. Chem. 1996, 61, 7244-7245, and references therein.
    • For the chirality transfer via a chiral borane-amine adduct in alkylation of (S) -N-benzylproline methyl ester, see: Ferey, V.; Vedrenne, P.; Toupet, L.; Le Gall, T.; Mioskowski, C. J. Org. Chem. 1996, 61, 7244-7245, and references therein.
  • 22
    • 64349114516 scopus 로고    scopus 로고
    • Compound la was prepared from commercially available N, N- dimethyl L-prolineamide.
    • Compound la was prepared from commercially available N, N- dimethyl L-prolineamide.
  • 23
    • 64349113459 scopus 로고    scopus 로고
    • Similar rearrangement at 60 °C gave 2a in 82% yield and 90:10 er.
    • Similar rearrangement at 60 °C gave 2a in 82% yield and 90:10 er.
  • 24
    • 0001232346 scopus 로고    scopus 로고
    • This is believed to arise from a preferential N pyramidal form, in which the substituent on nitrogen and the C-2 substituent are trans disposed. See: Vedejs, E, Arco, M. J, Powell, D. W, Renga, J. M; Singer, S. P. J. Org. Chem. 1978, 43, 4831-4837
    • This is believed to arise from a preferential N pyramidal form, in which the substituent on nitrogen and the C-2 substituent are trans disposed. See: Vedejs, E.; Arco, M. J.; Powell, D. W.; Renga, J. M; Singer, S. P. J. Org. Chem. 1978, 43, 4831-4837.
  • 26
    • 33847000590 scopus 로고    scopus 로고
    • For the case with chiral Lewis acid, see: a
    • For the case with chiral Lewis acid, see: (a) Blid, J.; Panknin, O.; Tuzina, P.; Somfai, P. J. Org. Chem. 2007, 72, 1294.
    • (2007) J. Org. Chem , vol.72 , pp. 1294
    • Blid, J.1    Panknin, O.2    Tuzina, P.3    Somfai, P.4
  • 28
    • 64349112197 scopus 로고    scopus 로고
    • The enantiomeric ratio of 2a was determined by HPLC using a Chiracel OD-H column.
    • The enantiomeric ratio of 2a was determined by HPLC using a Chiracel OD-H column.
  • 29
    • 44849127029 scopus 로고    scopus 로고
    • For fluorescent anthracene-based amino acid derivatives, see
    • For fluorescent anthracene-based amino acid derivatives, see: Kohta, S.; Shah, V. R.; Mishra, P. P.; Datta, A. Amino Acids 2007, 35, 169-173.
    • (2007) Amino Acids , vol.35 , pp. 169-173
    • Kohta, S.1    Shah, V.R.2    Mishra, P.P.3    Datta, A.4
  • 30
    • 36448968253 scopus 로고    scopus 로고
    • For a study on efficient incorporation of fluorescent nonnatural amino acids, see: a
    • For a study on efficient incorporation of fluorescent nonnatural amino acids, see: (a) Doi, Y.; Ohtsuki, T.; Shimizu, Y.; Ueda, T.; Sisido, M. J. Am. Chem. Soc. 2007, 129, 14458-14462.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 14458-14462
    • Doi, Y.1    Ohtsuki, T.2    Shimizu, Y.3    Ueda, T.4    Sisido, M.5
  • 32
    • 0034346844 scopus 로고    scopus 로고
    • Only one example of [1, 2]-Stevens rearrangement of an ammonium salt containing a thienylmethyl moiety has been reported. See: Kocharyan, S. T.; Karapetyan, V. E.; Churkina, N. P. Russ. J. Gen. Chem. 2000, 70, 1094-1097.
    • Only one example of [1, 2]-Stevens rearrangement of an ammonium salt containing a thienylmethyl moiety has been reported. See: Kocharyan, S. T.; Karapetyan, V. E.; Churkina, N. P. Russ. J. Gen. Chem. 2000, 70, 1094-1097.
  • 34
    • 0028244615 scopus 로고    scopus 로고
    • 2O)). See: Genin, M. J.; Baures, P. W.; Johnson, R. L. Tetrahedron Lett. 1994, 35, 4967-4968.
    • 2O)). See: Genin, M. J.; Baures, P. W.; Johnson, R. L. Tetrahedron Lett. 1994, 35, 4967-4968.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.