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Volumn 74, Issue 9, 2009, Pages 3414-3423

Cross-metathesis reactions as an efficient tool in the synthesis of fluorinated cyclic β-amino acids

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC HYDROGENATION; CHEMICAL REDUCTION; CHIRAL AUXILIARIES; CROSS METATHESIS; DIASTEREOSELECTIVE; DIFLUORINATED; IMIDOYL CHLORIDE; OPTIMAL REACTION CONDITION; RING SIZES; UNSATURATED ESTERS;

EID: 66449131204     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900296d     Document Type: Article
Times cited : (39)

References (87)
  • 12
    • 0035385142 scopus 로고    scopus 로고
    • Fülöp, F. Chem. Rev. 2001, 101, 2181-2204.
    • (2001) Chem. Rev , vol.101 , pp. 2181-2204
    • Fülöp, F.1
  • 18
    • 0028130028 scopus 로고
    • (b) Cole, D. C. Tetrahedron 1994, 50, 9517-9582.
    • (1994) Tetrahedron , vol.50 , pp. 9517-9582
    • Cole, D.C.1
  • 19
    • 66449134085 scopus 로고    scopus 로고
    • EnantioselectiVe Synthesis of -Amino Acids; 2nd ed.; Juaristi, E. C., Soloshonok, V. A., Eds.; Wiley-VCH Ltd.: New York, 2005.
    • (c) EnantioselectiVe Synthesis of -Amino Acids; 2nd ed.; Juaristi, E. C., Soloshonok, V. A., Eds.; Wiley-VCH Ltd.: New York, 2005.
  • 23
    • 38149016915 scopus 로고    scopus 로고
    • See, for example: a
    • See, for example: (a) O'Hagan, D. Chem. Soc. Rev. 2008, 37, 308-319.
    • (2008) Chem. Soc. Rev , vol.37 , pp. 308-319
    • O'Hagan, D.1
  • 49
    • 53849119880 scopus 로고    scopus 로고
    • Fustero, S.; Sánchez-Roselló, M.; Rodrigo, V.; Sanz-Cervera, J. F.; Piera, J.; Simón-Fuentes, A.; del Pozo, C. Chem.sEur. J. 2008, 14, 7019-7029.
    • (d) Fustero, S.; Sánchez-Roselló, M.; Rodrigo, V.; Sanz-Cervera, J. F.; Piera, J.; Simón-Fuentes, A.; del Pozo, C. Chem.sEur. J. 2008, 14, 7019-7029.
  • 50
    • 0002703568 scopus 로고    scopus 로고
    • It should be noted that fluorinated imidoyl halides constitute readily available building blocks for the synthesis of a variety of fluorine-containing molecules: (a) Uneyama, K. J. Fluorine Chem. 1999, 97, 11-25
    • It should be noted that fluorinated imidoyl halides constitute readily available building blocks for the synthesis of a variety of fluorine-containing molecules: (a) Uneyama, K. J. Fluorine Chem. 1999, 97, 11-25.
  • 57
    • 0007423482 scopus 로고
    • For leading references, see: d
    • For leading references, see: (d) Crowe, W. E.; Zhang, Z. J. J. Am. Chem. Soc. 1993, 115, 10998-10999.
    • (1993) J. Am. Chem. Soc , vol.115 , pp. 10998-10999
    • Crowe, W.E.1    Zhang, Z.J.2
  • 73
    • 66449094507 scopus 로고    scopus 로고
    • Purification of cross-coupled products 3a-c by means of column chromatography was hampered by the difficult separation of ester homodimers 8.
    • Purification of cross-coupled products 3a-c by means of column chromatography was hampered by the difficult separation of ester homodimers 8.
  • 74
    • 3943048796 scopus 로고    scopus 로고
    • For a review, see
    • For a review, see: Schmidt, B. Eur. J. Org. Chem. 2004, 1865-1880.
    • (2004) Eur. J. Org. Chem , pp. 1865-1880
    • Schmidt, B.1
  • 75
    • 66449115076 scopus 로고    scopus 로고
    • The isomerization of the double bond in the reaction of 1a with acrylates was thwarted by an electronic effect of the CF2 group. For a mechanistic explanation, see ref 15a
    • The isomerization of the double bond in the reaction of 1a with acrylates was thwarted by an electronic effect of the CF2 group. For a mechanistic explanation, see ref 15a.
  • 76
    • 66449134662 scopus 로고    scopus 로고
    • The same reaction in the presence of first-generation Grubbs catalyst I afforded only 20% of homodimer 7 after 48 h.
    • The same reaction in the presence of first-generation Grubbs catalyst I afforded only 20% of homodimer 7 after 48 h.
  • 78
    • 66449132712 scopus 로고    scopus 로고
    • See ref 17
    • (b) See ref 17.
  • 79
    • 66449111204 scopus 로고    scopus 로고
    • The enantioselective hydrogenation of five-membered enamino ester 11a with a ruthenium catalyst [Ru(COD)(Methallyl)2] and a chiral ligand [(S)-BINAP] was also attempted with no success.
    • The enantioselective hydrogenation of five-membered enamino ester 11a with a ruthenium catalyst [Ru(COD)(Methallyl)2] and a chiral ligand [(S)-BINAP] was also attempted with no success.
  • 81
    • 66449083976 scopus 로고    scopus 로고
    • In this reaction, an 86:14 mixture of the cisdiastereoisomers was obtained.
    • In this reaction, an 86:14 mixture of the cisdiastereoisomers was obtained.
  • 82
    • 66449109592 scopus 로고    scopus 로고
    • For the X-ray structure of, -13, see ref 18
    • For the X-ray structure of (+)-13, see ref 18.
  • 83
    • 66449111492 scopus 로고    scopus 로고
    • In this manner, the chiral auxiliary 8-phenylmenthol was also recovered 70-80
    • In this manner, the chiral auxiliary 8-phenylmenthol was also recovered (70-80%).
  • 85
    • 66449112919 scopus 로고    scopus 로고
    • See ref 3
    • (b) See ref 3.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.