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Volumn 74, Issue 8, 2009, Pages 3217-3220

Expedient preparation of all isomers of 2-aminocyclobutanecarboxylic acid in enantiomerically pure form

Author keywords

[No Author keywords available]

Indexed keywords

EPIMERIZATION; FACILE ACCESS; GRAM SCALE; HIGH YIELDS;

EID: 65249128754     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900175p     Document Type: Article
Times cited : (47)

References (30)
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    • Reviews: a
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    • (2001) Chem. Rev , vol.101 , pp. 2181-2204
    • Fülöp, F.1
  • 7
    • 65249135346 scopus 로고    scopus 로고
    • Recent patents: (a) Zenkoh, T.; Nozawa, E.; Matsuura, K.; Seo, R. Chem. Abstr. 2008, 149, 471824.
    • Recent patents: (a) Zenkoh, T.; Nozawa, E.; Matsuura, K.; Seo, R. Chem. Abstr. 2008, 149, 471824.
  • 10
    • 0003693460 scopus 로고    scopus 로고
    • 2nd ed, Juaristi, E, Soloshonok, V. A, Eds, Wiley-VCH: Weinheim, Germany
    • (a) Enantioselective Synthesis of fi-Amino Acids, 2nd ed.; Juaristi, E., Soloshonok, V. A., Eds.; Wiley-VCH: Weinheim, Germany, 2005.
    • (2005) Enantioselective Synthesis of fi-Amino Acids
  • 12
    • 14044251506 scopus 로고    scopus 로고
    • For reviews which include particular mention of cyclobutane β-amino acids, see: a
    • For reviews which include particular mention of cyclobutane β-amino acids, see: (a) Ortuño, R. M.; Moglioni, A. G.; Moltrasio, G. Y. Curr. Org. Chem. 2005, 9, 237-259.
    • (2005) Curr. Org. Chem , vol.9 , pp. 237-259
    • Ortuño, R.M.1    Moglioni, A.G.2    Moltrasio, G.Y.3
  • 13
    • 84891300630 scopus 로고    scopus 로고
    • 2nd ed, Juaristi, E, Soloshonok, V. A, Eds, Wiley-VCH: Weinheim, Germany, Chapter 5, pp
    • (b) Ortuño, R. M. In Enantioselective Synthesis of β-Amino Acids, 2nd ed.; Juaristi, E., Soloshonok, V. A., Eds.; Wiley-VCH: Weinheim, Germany, 2005; Chapter 5, pp 117-137.
    • (2005) Enantioselective Synthesis of β-Amino Acids , pp. 117-137
    • Ortuño, R.M.1
  • 18
    • 38349102187 scopus 로고    scopus 로고
    • For a recent review on the desymmetrization of cyclic meso-anhydrides, see
    • For a recent review on the desymmetrization of cyclic meso-anhydrides, see: Atodiresei, I.; Schiffers, I.; Bolm, C. Chem. Rev. 2007, 107, 5683-5712.
    • (2007) Chem. Rev , vol.107 , pp. 5683-5712
    • Atodiresei, I.1    Schiffers, I.2    Bolm, C.3
  • 29
    • 8144230852 scopus 로고    scopus 로고
    • The possibility of epimerization of 4 or 5 to give trans-isomers was considered. In a series of tests, however, 4a/4b mixtures were recovered completely unreacted from basic aqueous conditions, or extensively degraded when treated with t-BuOK/THF at reflux. For a related use of these latter conditions, see: Priego, J.; Flores, P.; Ortiz-Nava, C; Escalante, J. Tetrahedron: Asymmetry 2004, 15, 3545-3549.
    • The possibility of epimerization of 4 or 5 to give trans-isomers was considered. In a series of tests, however, 4a/4b mixtures were recovered completely unreacted from basic aqueous conditions, or extensively degraded when treated with t-BuOK/THF at reflux. For a related use of these latter conditions, see: Priego, J.; Flores, P.; Ortiz-Nava, C; Escalante, J. Tetrahedron: Asymmetry 2004, 15, 3545-3549.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.