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Volumn 8, Issue 22, 2006, Pages 5109-5112

Synthesis and application of quinazoline-oxazoline-containing (Quinazox) ligands

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Indexed keywords


EID: 33750924793     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062023+     Document Type: Article
Times cited : (53)

References (50)
  • 4
    • 0003445429 scopus 로고    scopus 로고
    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: New York
    • (a) Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: New York, 1999.
    • (1999) Comprehensive Asymmetric Catalysis
  • 6
    • 33750923564 scopus 로고    scopus 로고
    • Ligbank (www.ligbank.com), the European Ligand Bank, provides a venue for the exchange of ligands between interested research groups. This initiative is expected to facilitate matching optimal ligand structures with a particular asymmetric transformation.
  • 22
    • 33750901684 scopus 로고    scopus 로고
    • note
    • Following a well-established tradition, we assigned the name Quinazox to a class of ligands with the general structure 3.
  • 29
    • 33744482299 scopus 로고    scopus 로고
    • and references therein
    • For examples of oxazoline-containing axially chiral bidentate ligands, see: Zhang, W.; Xie, F.; Yoshinaga, H.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Synlett 2006, 8, 1185-1188 and references therein.
    • (2006) Synlett , vol.8 , pp. 1185-1188
    • Zhang, W.1    Xie, F.2    Yoshinaga, H.3    Kida, T.4    Nakatsuji, Y.5    Ikeda, I.6
  • 32
    • 33750908454 scopus 로고    scopus 로고
    • note
    • Although 11 is commercially available, its high cost makes its synthesis from inexpensive 9 an attractive alternative, especially for large-scale preparations of acyl chloride 10.
  • 34
    • 0034549484 scopus 로고    scopus 로고
    • For an alternative, four-step synthesis of 8 from ethyl isobutyrate that we used in our exploratory studies, see: Hayashi, Y.; Orikasa, S.; Tanaka, K.; Kanoh, K.; Kiso, Y. J. Org. Chem. 2000, 65, 8402-8405.
    • (2000) J. Org. Chem. , vol.65 , pp. 8402-8405
    • Hayashi, Y.1    Orikasa, S.2    Tanaka, K.3    Kanoh, K.4    Kiso, Y.5
  • 42
    • 33750915493 scopus 로고    scopus 로고
    • note
    • 2, the most commonly used activator for the formation of 2-oxazolines from nitriles, proved ineffective. Only complexation of Zn(II) with 22 (in itself a potentially tridentate ligand) was noted.
  • 43
    • 33750912470 scopus 로고    scopus 로고
    • note
    • 2 = 0.0767 (all data).
  • 49
    • 33750919982 scopus 로고    scopus 로고
    • note
    • 2 and LiOAc are the optimal solvent and base, respectively, leading to an improved enantiopurity of 28.
  • 50
    • 33750903374 scopus 로고    scopus 로고
    • note
    • 2, KOAc), the reaction furnished 28 in 21% ee (R). This, combined with other results (Table 1, entries 2 and 4), indicates that the rates of the AAA reaction for the two diastereomers are very similar.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.