Stereoselective synthesis of Baylis-Hillman-type adducts via allenolates generated by acyl migration

Organic Letters

Volumn 6, Issue 22, 2004, Pages 4005-4008

  Gudimalla, Nagaraju ^a   Fröhlich, Roland ^a   Hoppe, Dieter ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALDOL REACTION; ARTICLE; BAYLIS HILLMAN REACTION; CHEMICAL BOND; CYCLIZATION; STEREOCHEMISTRY;

EID: 8744297169     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0483908     Document Type: Article

References (46)

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34. In some examples, enone (E)-12 and (Z)-adducts (<2%) were isolated after aqueous workup.
35. In the (E)-configured adducts a NOE between the olefinic proton and the methyl groups adjacent to the carbamate group is present, whereas in the (Z)-configured adducts a NOE between the olefinic proton and the benzyl proton is observed.
36. -3, hydrogens calculated and refined as riding atoms. Data sets were collected with a Nonius KappaCCD diffractometer. Programs used: data collection COLLECT (Nonius B.V., 1998), data reduction Denzo-SMN (Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307), absorption correction SORTAV (Blessing, R. H. Acta Crystallogr. 1995, A51, 33. Blessing, R. H. J. Appl. Crystallogr. 1997, 30, 421), structure solution SHELXS-97 (Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467), structure refinement SHELXL-97 (Sheldrick, G. M. Universität Göttingen, 1997), graphics Diamond (Brandenburg, K. Universität Bonn, 1997).
37. -3, hydrogens calculated and refined as riding atoms. Data sets were collected with a Nonius KappaCCD diffractometer. Programs used: data collection COLLECT (Nonius B.V., 1998), data reduction Denzo-SMN (Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307), absorption correction SORTAV (Blessing, R. H. Acta Crystallogr. 1995, A51, 33. Blessing, R. H. J. Appl. Crystallogr. 1997, 30, 421), structure solution SHELXS-97 (Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467), structure refinement SHELXL-97 (Sheldrick, G. M. Universität Göttingen, 1997), graphics Diamond (Brandenburg, K. Universität Bonn, 1997).
38. -3, hydrogens calculated and refined as riding atoms. Data sets were collected with a Nonius KappaCCD diffractometer. Programs used: data collection COLLECT (Nonius B.V., 1998), data reduction Denzo-SMN (Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307), absorption correction SORTAV (Blessing, R. H. Acta Crystallogr. 1995, A51, 33. Blessing, R. H. J. Appl. Crystallogr. 1997, 30, 421), structure solution SHELXS-97 (Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467), structure refinement SHELXL-97 (Sheldrick, G. M. Universität Göttingen, 1997), graphics Diamond (Brandenburg, K. Universität Bonn, 1997).
39. -3, hydrogens calculated and refined as riding atoms. Data sets were collected with a Nonius KappaCCD diffractometer. Programs used: data collection COLLECT (Nonius B.V., 1998), data reduction Denzo-SMN (Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307), absorption correction SORTAV (Blessing, R. H. Acta Crystallogr. 1995, A51, 33. Blessing, R. H. J. Appl. Crystallogr. 1997, 30, 421), structure solution SHELXS-97 (Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467), structure refinement SHELXL-97 (Sheldrick, G. M. Universität Göttingen, 1997), graphics Diamond (Brandenburg, K. Universität Bonn, 1997).
40. -3, hydrogens calculated and refined as riding atoms. Data sets were collected with a Nonius KappaCCD diffractometer. Programs used: data collection COLLECT (Nonius B.V., 1998), data reduction Denzo-SMN (Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307), absorption correction SORTAV (Blessing, R. H. Acta Crystallogr. 1995, A51, 33. Blessing, R. H. J. Appl. Crystallogr. 1997, 30, 421), structure solution SHELXS-97 (Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467), structure refinement SHELXL-97 (Sheldrick, G. M. Universität Göttingen, 1997), graphics Diamond (Brandenburg, K. Universität Bonn, 1997).
41. -3, hydrogens calculated and refined as riding atoms. Data sets were collected with a Nonius KappaCCD diffractometer. Programs used: data collection COLLECT (Nonius B.V., 1998), data reduction Denzo-SMN (Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307), absorption correction SORTAV (Blessing, R. H. Acta Crystallogr. 1995, A51, 33. Blessing, R. H. J. Appl. Crystallogr. 1997, 30, 421), structure solution SHELXS-97 (Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467), structure refinement SHELXL-97 (Sheldrick, G. M. Universität Göttingen, 1997), graphics Diamond (Brandenburg, K. Universität Bonn, 1997).
42. In the case of furfural (entry 8), the (Z) adduct is formed irrespective of the condition at which the reaction is performed.
43. (a) Hamelin, O.; Wang, J.; Deprés, J. P.; Greene, A. E. Angew. Chem. 2000, 112, 4484; Angew. Chem., Int. Ed. 2000, 39, 4313.
44. (a) Hamelin, O.; Wang, J.; Deprés, J. P.; Greene, A. E. Angew. Chem. 2000, 112, 4484; Angew. Chem., Int. Ed. 2000, 39, 4313.
45. (b) Wang, W.; Digits, C. A.; Hatada, M.; Narula, S.; Rozamus, L. W.; Huestis, C. M.; Wong, J.; Dalgarno, D.; Holt, D. A. Org. Lett. 1999, 1, 2033.
46. -3, hydrogens calculated and refined as riding atoms.