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Volumn 68, Issue 1, 2003, Pages 3-10

The preparation and utility of bis(sulfinyl)imidoamidine ligands for the copper-catalyzed Diels-Alder reaction

Author keywords

[No Author keywords available]

Indexed keywords

LIGANDS;

EID: 0037427990     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020524c     Document Type: Article
Times cited : (87)

References (43)
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    • Other catalysts based on chirality solely at sulfur have been developed. (a) Khiar, N.; Fernandez, I.; Alcudia, F. Tetrahedron Lett. 1993, 34, 123-126. (b) Tokunoh, R.; Sodeoka, M.; Aoe, K.; Shibasaki, M. Tetrahedron Lett. 1995, 44, 8035-8038. (c) Bolm, C.; Kaugmann, D.; Zehnder, M.; Neuburger, M. A. Tetrahedron Lett. 1996, 37, 3985-3988. (d) Hiroi, K.; Suzuki, Y.; Kawagishi, R. Tetrahedron Lett. 1999, 40, 715-718. (e) Bolm, C.; Simic, O. J. Am. Chem. Soc. 2001, 123, 3830-3831. (f) Harmata, M.; Ghosh, S. K. Org. Lett. 2001, 3, 3321-3323.
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    • Other catalysts based on chirality solely at sulfur have been developed. (a) Khiar, N.; Fernandez, I.; Alcudia, F. Tetrahedron Lett. 1993, 34, 123-126. (b) Tokunoh, R.; Sodeoka, M.; Aoe, K.; Shibasaki, M. Tetrahedron Lett. 1995, 44, 8035-8038. (c) Bolm, C.; Kaugmann, D.; Zehnder, M.; Neuburger, M. A. Tetrahedron Lett. 1996, 37, 3985-3988. (d) Hiroi, K.; Suzuki, Y.; Kawagishi, R. Tetrahedron Lett. 1999, 40, 715-718. (e) Bolm, C.; Simic, O. J. Am. Chem. Soc. 2001, 123, 3830-3831. (f) Harmata, M.; Ghosh, S. K. Org. Lett. 2001, 3, 3321-3323.
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    • Other catalysts based on chirality solely at sulfur have been developed. (a) Khiar, N.; Fernandez, I.; Alcudia, F. Tetrahedron Lett. 1993, 34, 123-126. (b) Tokunoh, R.; Sodeoka, M.; Aoe, K.; Shibasaki, M. Tetrahedron Lett. 1995, 44, 8035-8038. (c) Bolm, C.; Kaugmann, D.; Zehnder, M.; Neuburger, M. A. Tetrahedron Lett. 1996, 37, 3985-3988. (d) Hiroi, K.; Suzuki, Y.; Kawagishi, R. Tetrahedron Lett. 1999, 40, 715-718. (e) Bolm, C.; Simic, O. J. Am. Chem. Soc. 2001, 123, 3830-3831. (f) Harmata, M.; Ghosh, S. K. Org. Lett. 2001, 3, 3321-3323.
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    • Other catalysts based on chirality solely at sulfur have been developed. (a) Khiar, N.; Fernandez, I.; Alcudia, F. Tetrahedron Lett. 1993, 34, 123-126. (b) Tokunoh, R.; Sodeoka, M.; Aoe, K.; Shibasaki, M. Tetrahedron Lett. 1995, 44, 8035-8038. (c) Bolm, C.; Kaugmann, D.; Zehnder, M.; Neuburger, M. A. Tetrahedron Lett. 1996, 37, 3985-3988. (d) Hiroi, K.; Suzuki, Y.; Kawagishi, R. Tetrahedron Lett. 1999, 40, 715-718. (e) Bolm, C.; Simic, O. J. Am. Chem. Soc. 2001, 123, 3830-3831. (f) Harmata, M.; Ghosh, S. K. Org. Lett. 2001, 3, 3321-3323.
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    • note
    • Addition of methylamine to 18 followed by deprotonation and addition to imidate 13 did not provide the desired product 17.
  • 28
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    • For the addition of Grignard reagents into p-toluenesulfinyl imines, attack at sulfur competes with attack at the carbon-nitrogen double bond. Moreau, P.; Essiz, M.; Merour, J.; Bouzard, D. Tetrahedron: Asymmetry 1997, 8, 591-594. Attack at sulfur is not observed for tert-butanesulfinyl imines. See ref 4a.
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    • note
    • The ligand crystallizes as a pair of molecules in the asymmetric unit. The dihedral angles are 9.0° and 9.7° for one molecule and 4.4° and 15.6° in the other. See Supporting Information for crystallographic data.
  • 37
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    • note
    • Electrospray ionization in MeCN showed diagnostic isotopic distributions consistent with the presence of the above species (see Supporting Information).
  • 43
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    • note
    • While not strictly necessary, better and more reproducible results were found when molecular sieves were added to the reaction mixture. For example, compound 25b is produced in only 69% ee in the absence of molecular sieves.


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