Cycloadducts from highly functionalized nitrones and oximes as ligands in the enantioselective addition of diethylzinc to benzaldehyde

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 22, 1998, Pages 3717-3724

  Baskaran, Subramanian ^a   Aurich, Hans Günter ^a   Biesemeier, Frank ^a   Harms, Klaus ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748737594     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a806744i     Document Type: Article

References (29)

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2. (b) G. Procter, Asymmetric Synthesis, Oxford University Press, 1996, pp. 7-8;
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4. A collection of enantioselective catalysts derived from the chiral pool is given by H.-U. Blaser, Chem. Rev., 1992, 92, 935.
5. See for Instance (a) K. Soai and S. Niwa, Chem. Rev., 1992, 92, 833;
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10. See ref. (4) and references cited therein.
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12. (a) For preparation of the N-alkylhydroxylamines see ref. 4;
13. (b) It is obvious that for the conversion of compound 4 to the corresponding cycloadducts 8, the yield should be relatively low, since every step of the reaction sequence must take place twice.
14. S. Baskaran and H. G. Aurich, Synlett, 1998, 277.
15. (a) See for example W. Oppolzer and K. Keller, Tetrahedron Lett., 1970, 1117;
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22. 1H NMR signal for 5-H. For a direct comparison of analogous compounds of type 17 and 19 see for example, ref. 11(a), in which the data of compounds 12Ba and Ca should be compared with those of 21Ba and Ca, respectively.
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24. calc is good, even though the Karplus equation was established for carbocyclic rather than heterocyclic compounds.
25. α-H's are those which are cis-orientated to 1-H, α-H's are those which are trans-orientated.
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27. H. G. Aurich and M. Geiger, unpublished results; M. Geiger, Dissertation, University of Marburg, Germany, 1997.
28. G. M. Sheldrick, SHELXS-97 Program for the solution of crystal structures, Göttingen, 1997.
29. G. M. Sheldrick, SHELXL-97 Program for the Refinement of Crystal Structures, Göttingen, 1997.