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Volumn , Issue 5, 1998, Pages 483-486

Asymmetric palladium(0) catalyzed tandem alkylation and SN′ cyclization of 1,4-dichlorobut-2-ene by chiral imines of aminoacetonitrile for the total synthesis of 1-aminocyclopropanecarboxylic acids

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EID: 0002433821     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1687     Document Type: Article
Times cited : (14)

References (36)
  • 10
    • 37049109787 scopus 로고
    • 2, 70°C for 1 h then 1°C per min: retention times, 111.19 and 117.13 min, respectively). For the first use of (1S,25,5S)-2-hydroxypinan-3-one as chiral auxiliary see: Yamada, S.I.; Oguri, T.; Shioiri, T. J. Chem. Soc. Chem. Commun. 1976, 136-137.
    • (1976) J. Chem. Soc. Chem. Commun. , pp. 136-137
    • Yamada, S.I.1    Oguri, T.2    Shioiri, T.3
  • 11
    • 85083132845 scopus 로고    scopus 로고
    • note
    • 3).
  • 12
    • 85083153030 scopus 로고    scopus 로고
    • note
    • N′ cyclization of E -and Z-1 by racemic imine 2, required two equiv of NaH, but with the imines (-)- and (+)-8a derived from (-)- and (+)-hydroxypinanones, respectively, at least three equiv of base were obviously required.
  • 13
    • 0001597606 scopus 로고
    • HMPA as co-solvent is well known for its ability to accelerate nucleophilic reactions. See for instance Pfiffer, P.E.; Silbert, L.S. J. Org. Chem. 1970, 35, 262.
    • (1970) J. Org. Chem. , vol.35 , pp. 262
    • Pfiffer, P.E.1    Silbert, L.S.2
  • 14
    • 85083131611 scopus 로고    scopus 로고
    • note
    • 3).
  • 16
    • 85083120490 scopus 로고    scopus 로고
    • note
    • 2 108.0687, found 108.0679.
  • 22
    • 0002822594 scopus 로고
    • The pKa values of malononitrile and diethylmalonate are 11.2 and 13.3, respectively (Wada, M.; Mitsunobu, O. Tetrahedron Lett. 1972, 1279).
    • (1972) Tetrahedron Lett. , pp. 1279
    • Wada, M.1    Mitsunobu, O.2
  • 27
    • 85083141288 scopus 로고    scopus 로고
    • note
    • 3]; the others were based on HPLC chromatography (1) or on X-ray analysis (1).
  • 28
    • 85083137192 scopus 로고    scopus 로고
    • note
    • 2, 55°C) two peaks at 52.75 (34%) and 55.83 (66%) min; while after re-treatment in the presence of (R)-BINAP-Pd(0), E-13a (9% ee) displayed two peaks at 52.74 (55%) and 56 (45%) min.


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