Asymmetric synthesis of allylic sulfides via palladium-mediated allylation of thiols

Tetrahedron Asymmetry

Volumn 9, Issue 19, 1998, Pages 3353-3357

  Frank, Michael ^a   Gais, Hans Joachim ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; PALLADIUM; SULFIDE; THIOL DERIVATIVE;

CATALYSIS; ENANTIOMER; GAS CHROMATOGRAPHY; LIGAND BINDING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REVIEW; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032476145     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00345-0     Document Type: Article

References (34)

1. Gais, H.-J.; Eichelmann, H.; Spalthoff, N.; Gerhards, F.; Frank, M.; Raabe, G. Tetrahedron: Asymmetry 1998, 9, 235-248.
2. For the palladium-mediated synthesis of racemic allylic sulfides by using achiral ligands, see: (a) Inoue, Y.; Taguchi, M.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1985, 58, 2721-2722. (b) Auburn, P. R.; Whelan, J.; Bosnich, B. J. Chem. Soc., Chem. Commun. 1986, 146-147. (c) Trost, B. M.; Scanlan, T. S. Tetrahedron Lett. 1986, 27, 4141-4144. (d) Deardorff, D. R.; Linde II, R. G.; Martin, A. M.; Shulman, M. J. J. Org. Chem. 1989, 54, 2759-2762. (e) Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1992, 33, 8099-8102. (f) Moreno-Mañas, M.; Pleixats, R.; Villarroya, M. Tetrahedron 1993, 49, 1457-1464. (g) Arredondo, Y.; Moreno-Mañas, M.; Pleixats, R.; Villarroya, M. Tetrahedron 1993, 49, 1465-1470. (h) Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron 1994, 50, 10321-10330.
3. For the palladium-mediated synthesis of racemic allylic sulfides by using achiral ligands, see: (a) Inoue, Y.; Taguchi, M.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1985, 58, 2721-2722. (b) Auburn, P. R.; Whelan, J.; Bosnich, B. J. Chem. Soc., Chem. Commun. 1986, 146-147. (c) Trost, B. M.; Scanlan, T. S. Tetrahedron Lett. 1986, 27, 4141-4144. (d) Deardorff, D. R.; Linde II, R. G.; Martin, A. M.; Shulman, M. J. J. Org. Chem. 1989, 54, 2759-2762. (e) Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1992, 33, 8099-8102. (f) Moreno-Mañas, M.; Pleixats, R.; Villarroya, M. Tetrahedron 1993, 49, 1457-1464. (g) Arredondo, Y.; Moreno-Mañas, M.; Pleixats, R.; Villarroya, M. Tetrahedron 1993, 49, 1465-1470. (h) Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron 1994, 50, 10321-10330.
4. For the palladium-mediated synthesis of racemic allylic sulfides by using achiral ligands, see: (a) Inoue, Y.; Taguchi, M.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1985, 58, 2721-2722. (b) Auburn, P. R.; Whelan, J.; Bosnich, B. J. Chem. Soc., Chem. Commun. 1986, 146-147. (c) Trost, B. M.; Scanlan, T. S. Tetrahedron Lett. 1986, 27, 4141-4144. (d) Deardorff, D. R.; Linde II, R. G.; Martin, A. M.; Shulman, M. J. J. Org. Chem. 1989, 54, 2759-2762. (e) Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1992, 33, 8099-8102. (f) Moreno-Mañas, M.; Pleixats, R.; Villarroya, M. Tetrahedron 1993, 49, 1457-1464. (g) Arredondo, Y.; Moreno-Mañas, M.; Pleixats, R.; Villarroya, M. Tetrahedron 1993, 49, 1465-1470. (h) Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron 1994, 50, 10321-10330.
5. For the palladium-mediated synthesis of racemic allylic sulfides by using achiral ligands, see: (a) Inoue, Y.; Taguchi, M.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1985, 58, 2721-2722. (b) Auburn, P. R.; Whelan, J.; Bosnich, B. J. Chem. Soc., Chem. Commun. 1986, 146-147. (c) Trost, B. M.; Scanlan, T. S. Tetrahedron Lett. 1986, 27, 4141-4144. (d) Deardorff, D. R.; Linde II, R. G.; Martin, A. M.; Shulman, M. J. J. Org. Chem. 1989, 54, 2759-2762. (e) Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1992, 33, 8099-8102. (f) Moreno-Mañas, M.; Pleixats, R.; Villarroya, M. Tetrahedron 1993, 49, 1457-1464. (g) Arredondo, Y.; Moreno-Mañas, M.; Pleixats, R.; Villarroya, M. Tetrahedron 1993, 49, 1465-1470. (h) Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron 1994, 50, 10321-10330.
6. For the palladium-mediated synthesis of racemic allylic sulfides by using achiral ligands, see: (a) Inoue, Y.; Taguchi, M.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1985, 58, 2721-2722. (b) Auburn, P. R.; Whelan, J.; Bosnich, B. J. Chem. Soc., Chem. Commun. 1986, 146-147. (c) Trost, B. M.; Scanlan, T. S. Tetrahedron Lett. 1986, 27, 4141-4144. (d) Deardorff, D. R.; Linde II, R. G.; Martin, A. M.; Shulman, M. J. J. Org. Chem. 1989, 54, 2759-2762. (e) Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1992, 33, 8099-8102. (f) Moreno-Mañas, M.; Pleixats, R.; Villarroya, M. Tetrahedron 1993, 49, 1457-1464. (g) Arredondo, Y.; Moreno-Mañas, M.; Pleixats, R.; Villarroya, M. Tetrahedron 1993, 49, 1465-1470. (h) Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron 1994, 50, 10321-10330.
7. For the palladium-mediated synthesis of racemic allylic sulfides by using achiral ligands, see: (a) Inoue, Y.; Taguchi, M.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1985, 58, 2721-2722. (b) Auburn, P. R.; Whelan, J.; Bosnich, B. J. Chem. Soc., Chem. Commun. 1986, 146-147. (c) Trost, B. M.; Scanlan, T. S. Tetrahedron Lett. 1986, 27, 4141-4144. (d) Deardorff, D. R.; Linde II, R. G.; Martin, A. M.; Shulman, M. J. J. Org. Chem. 1989, 54, 2759-2762. (e) Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1992, 33, 8099-8102. (f) Moreno-Mañas, M.; Pleixats, R.; Villarroya, M. Tetrahedron 1993, 49, 1457-1464. (g) Arredondo, Y.; Moreno-Mañas, M.; Pleixats, R.; Villarroya, M. Tetrahedron 1993, 49, 1465-1470. (h) Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron 1994, 50, 10321-10330.
8. For the palladium-mediated synthesis of racemic allylic sulfides by using achiral ligands, see: (a) Inoue, Y.; Taguchi, M.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1985, 58, 2721-2722. (b) Auburn, P. R.; Whelan, J.; Bosnich, B. J. Chem. Soc., Chem. Commun. 1986, 146-147. (c) Trost, B. M.; Scanlan, T. S. Tetrahedron Lett. 1986, 27, 4141-4144. (d) Deardorff, D. R.; Linde II, R. G.; Martin, A. M.; Shulman, M. J. J. Org. Chem. 1989, 54, 2759-2762. (e) Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1992, 33, 8099-8102. (f) Moreno-Mañas, M.; Pleixats, R.; Villarroya, M. Tetrahedron 1993, 49, 1457-1464. (g) Arredondo, Y.; Moreno-Mañas, M.; Pleixats, R.; Villarroya, M. Tetrahedron 1993, 49, 1465-1470. (h) Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron 1994, 50, 10321-10330.
9. For the palladium-mediated synthesis of racemic allylic sulfides by using achiral ligands, see: (a) Inoue, Y.; Taguchi, M.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1985, 58, 2721-2722. (b) Auburn, P. R.; Whelan, J.; Bosnich, B. J. Chem. Soc., Chem. Commun. 1986, 146-147. (c) Trost, B. M.; Scanlan, T. S. Tetrahedron Lett. 1986, 27, 4141-4144. (d) Deardorff, D. R.; Linde II, R. G.; Martin, A. M.; Shulman, M. J. J. Org. Chem. 1989, 54, 2759-2762. (e) Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1992, 33, 8099-8102. (f) Moreno-Mañas, M.; Pleixats, R.; Villarroya, M. Tetrahedron 1993, 49, 1457-1464. (g) Arredondo, Y.; Moreno-Mañas, M.; Pleixats, R.; Villarroya, M. Tetrahedron 1993, 49, 1465-1470. (h) Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron 1994, 50, 10321-10330.
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30. 3 (2 mol%) and DIOP (8 mol%) gave 9a (E:Z=24:1, 16% ee, 68% yield) and 9b (E:Z ≥99:1, 3% ee, 95% yield), respectively.
31. 3) (96% ee).
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