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Volumn 19, Issue 13, 2008, Pages 1572-1575

Chiral ligand 2-(2′-piperidinyl)pyridine: synthesis, resolution and application in asymmetric diethylzinc addition to aldehydes

Author keywords

[No Author keywords available]

Indexed keywords

2 (2' PIPERIDINYL)PYRIDINE; ALCOHOL; ALDEHYDE; DIETHYLZINC; PYRIDINE DERIVATIVE; TARTARIC ACID;

EID: 48949114888     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.06.005     Document Type: Article
Times cited : (26)

References (46)
  • 21
    • 48949121101 scopus 로고    scopus 로고
    • Gillespie, P.; Goodnow, R. A.; Kowalczyk, A.; Le, K.; Zhang, Q. US Patent Appl. Publ. 2007/0167622, 2007, 66pp.
    • Gillespie, P.; Goodnow, R. A.; Kowalczyk, A.; Le, K.; Zhang, Q. US Patent Appl. Publ. 2007/0167622, 2007, 66pp.
  • 35
    • 48949121094 scopus 로고    scopus 로고
    • note
    • 6) δ ppm 1.35 (q, J = 12.81, 12.72, 12.72 Hz, 1H), 1.53 (m, 1H), 1.76 (dd, J = 25.80, 12.78 Hz, 1H), 2.07 (s, 1H), 2.50 (s, 1H), 2.89 (d, J = 11.30 Hz, 1H), 3.02 (d, J = 13.45 Hz, 1H), 3.44 (d, J = 10.29 Hz, 1H), 3.55 (d, J = 13.55 Hz, 1H), 4.26 (s, 1H), 7.26 (m, 1H), 7.61 (d, J = 7.83 Hz, 1H), 7.81 (t, J = 7.38, 7.38 Hz, 1H), 8.51 (d, J = 4.13 Hz, 1H).
  • 36
    • 48949121093 scopus 로고    scopus 로고
    • note
    • Enantiomeric excess analysis was determined by HPLC with a Chiralcel-OD column at 254 nm (hexane/iPrOH in the ratio of 97/3, flow 0.5 mL/min; the retention time of (R)-2 was 17.6 min, while that of (S)-2 was 19.5 min).
  • 37
    • 48949121092 scopus 로고    scopus 로고
    • note
    • -3. X-ray data were collected with Bruker SMART APEX CCD diffractometer with graphite-monochromatized Mo Kα radiation (λ = 0.71073 Å) operated at 2.0 kW (50 kV, 40 mA). The structures were solved by direct methods with the program shelxs-97. All non-hydrogen atoms were refined anisotropically. The details of the crystallographic data have been deposited with Cambridge Crystallographic Data Centre as supplementary publication NO. CCDC 682454.


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