Stereoselective preparation and reaction of chiral secondary cycloalkyl- and alkyl-zinc reagents

Synlett

Volumn , Issue 12, 1998, Pages 1438-1440

  Boudier, Andreas ^a   Flachsmann, Felix ^a   Knochel, Paul ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001511282     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1951     Document Type: Article

References (17)

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5. (e) Zschage, O.; Hoppe, D. Tetrahedron 1992, 48, 5647;
6. (f) Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1991, 113, 9708.
7. Knochel, P.; Almena Perea, J. J.; Jones, P. Tetrahedron 1998, 54, 8275.
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12. 2 S in the appropriate stoichiometry: see Ref. 5.
13. Micouin, L.; Knochel, P. Synlett 1997, 327.
14. Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390.
15. (a) Brown, H. C.; Singaram, B. J Am. Chem. Soc., 1984, 106, 1797;
16. (b) Brown, H. C.; Prasad, J. V. N.; Gupta, A. K.; Bakshi, R. K. J. Org. Chem. 1987, 52, 310.
17. f = 0.25) affording 283 mg (41% based on the starting alkene) of pure 8c. The syn:anti ratio and enantioselectivity were determined by capillary GC analysis on a chiral β-cyclodextrin column (CP-Chirasil-Dex CB, Chrompack). A calibration was performed in each case with racemic material.