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Volumn 14, Issue 23, 2008, Pages 7019-7029

Solution-, solid-phase, and fluorous synthesis of β,β- difluorinated cyclic quaternary a-amino acid derivatives: A comparative study

Author keywords

Amino acids; Fluorous synthesis; Metathesis; Quaternary stereocenters; Solid phase synthesis

Indexed keywords

AMINATION; AMINO ACIDS; ESTERIFICATION; ESTERS; ETHERS; ORGANIC ACIDS; ORGANIC COMPOUNDS; ORGANOMETALLICS; SOLID SOLUTIONS;

EID: 53849119880     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200702009     Document Type: Article
Times cited : (32)

References (88)
  • 6
    • 53849120418 scopus 로고    scopus 로고
    • B. Baasner, H. Hagemann, J. C. Tatlow in Organo-Fluorine Compounds E 10 a-c, Thieme Stuttgart-New York, 2000;
    • a) B. Baasner, H. Hagemann, J. C. Tatlow in Organo-Fluorine Compounds Volume E 10 a-c, Thieme Stuttgart-New York, 2000;
  • 9
    • 0032546913 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 1998, 37, 1496-1513.
    • (1998) Angew. Chem. Int. Ed , vol.37 , pp. 1496-1513
  • 26
    • 33748999565 scopus 로고    scopus 로고
    • Preliminary results: S. Fustero, M. Sánchez-Roselló, V. Rodrigo, C. del Pozo, J. F. Sanz-Cervera, A. Simón, C. Ramírez de Arellano, Org. Lett. 2006, 8, 4129-4132.
    • Preliminary results: S. Fustero, M. Sánchez-Roselló, V. Rodrigo, C. del Pozo, J. F. Sanz-Cervera, A. Simón, C. Ramírez de Arellano, Org. Lett. 2006, 8, 4129-4132.
  • 31
    • 53849134703 scopus 로고    scopus 로고
    • 1H NMR integration of the crude mixtures were 10-20% higher.
    • 1H NMR integration of the crude mixtures were 10-20% higher.
  • 32
    • 0033550292 scopus 로고    scopus 로고
    • Compounds 5 are formed in this reaction as single isomers. A NOESY experiment performed on compound 5b showed an NOE between the benzylic hydrogens and the PMP hydrogens, which is only compatible with an E configuration for the O=N bond. Theoretical calculations have also predicted an E configuration for this kind of compounds. See: P. Bravo, S. Fustero, M. Guidetti, A. Volonterio, M. Zanda, J. Org. Chem. 1999, 64, 8731-8735.
    • Compounds 5 are formed in this reaction as single isomers. A NOESY experiment performed on compound 5b showed an NOE between the benzylic hydrogens and the PMP hydrogens, which is only compatible with an E configuration for the O=N bond. Theoretical calculations have also predicted an E configuration for this kind of compounds. See: P. Bravo, S. Fustero, M. Guidetti, A. Volonterio, M. Zanda, J. Org. Chem. 1999, 64, 8731-8735.
  • 33
    • 0038106171 scopus 로고    scopus 로고
    • For reviews of organometallic additions to imines see: a
    • For reviews of organometallic additions to imines see: a) R. Bloch, Chem. Rev. 1998, 98, 1407-1438;
    • (1998) Chem. Rev , vol.98 , pp. 1407-1438
    • Bloch, R.1
  • 39
  • 46
    • 53849108660 scopus 로고    scopus 로고
    • The allylzinc bromide must be freshly prepared and used immediately in order to obtain the results indicated above
    • The allylzinc bromide must be freshly prepared and used immediately in order to obtain the results indicated above.
  • 60
    • 53849115958 scopus 로고    scopus 로고
    • For the X-ray structure of (+)-11. see reference 15.
    • For the X-ray structure of (+)-11. see reference 15.
  • 64
    • 0001215147 scopus 로고
    • b) J. Gante, Angew. Chem. 1994, 106, 1780-1802;
    • (1994) Angew. Chem , vol.106 , pp. 1780-1802
    • Gante, J.1
  • 72
    • 0004127585 scopus 로고    scopus 로고
    • Eds, K. C. Nicolau, R. Hanko, W. Hartwig, Wiley-VCH, Weinheim, and 2;
    • d) Handbook of Combinatorial Chemistry (Eds.: K. C. Nicolau, R. Hanko, W. Hartwig), Wiley-VCH, Weinheim, 2002, Vol. 1 and 2;
    • (2002) Handbook of Combinatorial Chemistry , vol.1
  • 78
    • 84958634880 scopus 로고    scopus 로고
    • Eds, J. A. Gladysz, D. P. Curran, I. T. Horváth, Wiley-VCH, Weinheim
    • b) Handbook of Fluorous Chemistry (Eds.; J. A. Gladysz, D. P. Curran, I. T. Horváth), Wiley-VCH, Weinheim, 2004;
    • (2004) Handbook of Fluorous Chemistry
  • 79
    • 2942545969 scopus 로고    scopus 로고
    • c) W. Zhang, Chem. Rev. 2004, 104, 2531-2556.
    • (2004) Chem. Rev , vol.104 , pp. 2531-2556
    • Zhang, W.1
  • 84
    • 53849142025 scopus 로고    scopus 로고
    • As in the solution and solid-phase versions, when the allylzinc derived from ethyl 2-(bromomethyl)acrylate was used as nucleophile. the fluorous α-methylene γ-lactam 7 was isolated instead of the corresponding α-amino ester.
    • As in the solution and solid-phase versions, when the allylzinc derived from ethyl 2-(bromomethyl)acrylate was used as nucleophile. the fluorous α-methylene γ-lactam 7 was isolated instead of the corresponding α-amino ester.
  • 85
    • 84989499447 scopus 로고    scopus 로고
    • 2O did not work for the fluorous ester hydrolysis. Different transesterification methods such as the reaction with titanium tetraisopropoxide and isopropanol (D. Seebach, E. Hungerbühler, R. Naef, P. Schnurrenberger, B. Weidman, M. Züger, Synthesis 1982, 138-141)
    • 2O did not work for the fluorous ester hydrolysis. Different transesterification methods such as the reaction with titanium tetraisopropoxide and isopropanol (D. Seebach, E. Hungerbühler, R. Naef, P. Schnurrenberger, B. Weidman, M. Züger, Synthesis 1982, 138-141)
  • 86
    • 0001144457 scopus 로고    scopus 로고
    • or the reaction with benzyl bromide in the presence of 3-chloro-1-hydroxytetrabutyldistannoxane (CHTD) [a) J. Otera, T. Yano, R. Okawa, Organometallics 1986, 5, 1167-1170;
    • or the reaction with benzyl bromide in the presence of 3-chloro-1-hydroxytetrabutyldistannoxane (CHTD) [a) J. Otera, T. Yano, R. Okawa, Organometallics 1986, 5, 1167-1170;
  • 87
    • 33751500481 scopus 로고    scopus 로고
    • J. Otera, N. Dan-oh, H. Nozaki, J. Org. Chem. 1991, 56, 5307-5311] as catalyst also failed to remove the fluorous tag. In all these attempts, only starting material 19b was recovered unchanged.
    • b) J. Otera, N. Dan-oh, H. Nozaki, J. Org. Chem. 1991, 56, 5307-5311] as catalyst also failed to remove the fluorous tag. In all these attempts, only starting material 19b was recovered unchanged.
  • 88
    • 0003405157 scopus 로고    scopus 로고
    • The 2-(trimethylsilyl)ethyl group is widely employed for the protection of carboxylic acids because it is easily removed upon treatment with TBAF See:, 3rd. ed, Thieme. Stuttgart
    • The 2-(trimethylsilyl)ethyl group is widely employed for the protection of carboxylic acids because it is easily removed upon treatment with TBAF (See: P. J. Kocienski, Protecting Groups, 3rd. ed., Thieme. Stuttgart, 2005).
    • (2005) Protecting Groups
    • Kocienski, P.J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.