Application of chiral mixed phosphorus/sulfur ligands to palladium-catalyzed allylic substitutions

Journal of the American Chemical Society

Volumn 122, Issue 33, 2000, Pages 7905-7920

  Evans, David A ^a   Campos, Kevin R ^a   Tedrow, Jason S ^a   Michael, Forrest E ^a   Gagné, Michel R ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALLYL COMPOUND; BENZYLAMINE; LIGAND; MALONIC ACID DERIVATIVE; PALLADIUM; PHOSPHORUS; PIPERIDINE DERIVATIVE; PYRAN DERIVATIVE; SULFUR;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0034706036     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992543i     Document Type: Article

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57. It was believed that a more sterically demanding chiral pocket would increase the enantiomeric excess observed in the alkylation of 1,3-dimethylpropenyl acetate; however, using ligands containing bulkier phosphine substituents (33f and 33g) resulted in significantly lower enantioselectivities, 14% ee and 49% ee, respectively.
58. These substrates were reported to afford exclusive alkylation at the less substituted terminus. (a) Auburn, P. R.; Mackenzie, P. B.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2033-2046. (b) Dawson, G. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron: Asymmetry 1995, 6, 2535-2546 and references therein.
59. These substrates were reported to afford exclusive alkylation at the less substituted terminus. (a) Auburn, P. R.; Mackenzie, P. B.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2033-2046. (b) Dawson, G. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron: Asymmetry 1995, 6, 2535-2546 and references therein.
60. In contrast to most of the previously described allylic alkylations, these reactions showed no conversion at temperatures lower than room temperature.
61. No product was observed in the allylic alkylation of 34d.
62. Iida, T.; Yamamoto, N.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 4783-4784. Separation of enantiomers on the corresponding benzoate ester by HPLC analysis (Daicel Chiralcel AD) determined the enantiomeric excess to be >99%.
63. 1; a = 12.4686
64. 3; Z = 4; R = 0.0627, GoF = 1.019.
65. For an example of an X-ray crystal structuce of a single diastereomeric complex showing two diastereomers in solution by NMR, see: Berger, H.; Nesper, R.; Pregosin, P. S.; Rüegger, H.; Wörle, M. Helv. Chim. Acta 1993, 76, 1520-1538.
66. For an excellent reveiew on the structure and dynamics of chiral allyl complexes of Pd(II) see: Pregosin, P. S.; Salimann, R. Coord. Chem. Rev. 1996, 96, 35-68.
67. 3; Z = 4; R = 0.0386, GoF = 0.974.
68. Strongly rotated allyl moieties have been reported in crystal structures of various mixed donor ligand-palladium π-allyl complexes. (a) Albinati, A.; Pregosin, P. S.; Wick, K. Organometallics 1996, 15, 2419-21. (b) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031-1037. (c) Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelin, M.; Huttner, G.; Walter, O.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523-6.
69. Strongly rotated allyl moieties have been reported in crystal structures of various mixed donor ligand-palladium π-allyl complexes. (a) Albinati, A.; Pregosin, P. S.; Wick, K. Organometallics 1996, 15, 2419- 21. (b) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031-1037. (c) Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelin, M.; Huttner, G.; Walter, O.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523-6.
70. Strongly rotated allyl moieties have been reported in crystal structures of various mixed donor ligand-palladium π-allyl complexes. (a) Albinati, A.; Pregosin, P. S.; Wick, K. Organometallics 1996, 15, 2419- 21. (b) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031-1037. (c) Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelin, M.; Huttner, G.; Walter, O.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523-6.
71. 2 bond between Pd and C2-C3.
72. allyl(trans to S) = 5.48 ppm.
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74. Mackenzie, P. B.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2046-2054. For a review on Curtin-Hammett kinetics with numerous examples, see: Seeman, J. I. Chem. Rev. 1983, 83, 83-134.
75. Although the enantioselective allylic alkylation is difficult to accomplish, the substrate synthesis is quite facile by allylic oxidation of the desired cycloalkene. Hansson, S.; Heumann, A.; Rein, T.; Akermark, B. J. Org. Chem. 1990, 55, 975-984.
76. While Pd-sparteine complexes catalyze the allylic alkylation of 1,3-diphenylpropenyl acetate in 75% ee, the corresponding alkylation on cyclohexenyl acetate proceeds in only 50% ee. (a) Togni, A. Tetrahedron: Asymmetry 1991, 2, 683-690. Similarly, chiral phenanthroline complexes were found to catalyze the allylic alkylation of 1,3-diphenylpropenyl acetate in 92% ee, but the alkylation of cyclohexenyl acetate proceeds in only 16% ee. (b) Pena-Cabrera, E.; Norrby, P.; Sjögren, M.; Vitagliano, A.; de Felice, V.; Oslob, J.; Ishii, S.; O'Neill, D.; Akermark, B.; Helquist, P. J. Am. Chem. Soc. 1996, 118, 4299-4313.
77. While Pd-sparteine complexes catalyze the allylic alkylation of 1,3-diphenylpropenyl acetate in 75% ee, the corresponding alkylation on cyclohexenyl acetate proceeds in only 50% ee. (a) Togni, A. Tetrahedron: Asymmetry 1991, 2, 683-690. Similarly, chiral phenanthroline complexes were found to catalyze the allylic alkylation of 1,3-diphenylpropenyl acetate in 92% ee, but the alkylation of cyclohexenyl acetate proceeds in only 16% ee. (b) Pena-Cabrera, E.; Norrby, P.; Sjögren, M.; Vitagliano, A.; de Felice, V.; Oslob, J.; Ishii, S.; O'Neill, D.; Akermark, B.; Helquist, P. J. Am. Chem. Soc. 1996, 118, 4299-4313.
78. The ligands developed by Trost are effective for the allylic alkylation of both cyclic and acyclic substrates; however, only acyclic substrates containing sterically small substituents gave high enantiomeric excesses. (a) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089-4090. (b) Knuehl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845-1846 and references therein. Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1998, 37, 3047-3050.
79. The ligands developed by Trost are effective for the allylic alkylation of both cyclic and acyclic substrates; however, only acyclic substrates containing sterically small substituents gave high enantiomeric excesses. (a) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089-4090. (b) Knuehl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845-1846 and references therein. Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1998, 37, 3047-3050.
80. The ligands developed by Trost are effective for the allylic alkylation of both cyclic and acyclic substrates; however, only acyclic substrates containing sterically small substituents gave high enantiomeric excesses. (a) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089-4090. (b) Knuehl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845-1846 and references therein. Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1998, 37, 3047-3050.
81. 2 as the nucleophile in THF afforded good yields of 55a in 58% and 89% ee, respectively.
82. Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327-9343.
83. When ligands 10k and 11k were used in the allylic alkylation of 1,4-diacetoxycyclopentene, the monoalkylated adduct was obtained in 91% and 62% ee, respectively.
84. The most notable exception is the asymmetric palladium-catalyzed allylic substitution of cis-2,5-diacyloxy-2,5-dihydrofuran toward the synthesis of nucleosides. Trost, B. M.; Shi, Z. J. Am. Chem. Soc. 1996, 118, 3037-3038,
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89. 3; Z = 4; R = 0.0433, GoF = 1.282.
90. C1-C2 is shorter (1.36 Å) than C2-C3 (1.44 Å).
91. Geometry optimizations were performed at the PM3(tm) level using the Spartan Semiempirical Program 5.0 (Wavefunction Inc., Irvine, CA 92715) on a Silicon Graphics Impact 10000 (195 MHz, 128 M RAM) running IRIX 6.2. Calculations ere performed without counterions or solvent using these parameters: optcycle = 2000, maxcycle = 2000, charge = 0, multiplicity = 0. Calculations converged (energy difference between cycles <0.0005 kcal/mol) in ≤4 h CPU time.
92. 2 is small (<1.0 kcal/mol), making it difficult to (fetermine the nature of the drastic difference in the observed enantioselectivities in the allylic substitution of both acyclic and cyclic substrates.
93. The most notable example of a minor diastereomeric complex reacting faster than the major was reported by Halpem in the rhodium-catalyzed hydrogenation of (Z)-acetamidocinnamates. (a) Halpern, J. Science 1982, 217, 401 -407. (b) Halpern, J.; Landis, C. R. J. Am. Chem. Soc. 1987, 109, 1746-1754 and references therein.
94. The most notable example of a minor diastereomeric complex reacting faster than the major was reported by Halpem in the rhodium- catalyzed hydrogenation of (Z)-acetamidocinnamates. (a) Halpern, J. Science 1982, 217, 401 -407. (b) Halpern, J.; Landis, C. R. J. Am. Chem. Soc. 1987, 109, 1746-1754 and references therein.
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96. Evans, D. A.; Tedrow, J. S.; Michael, F. M.; Campos, K. R. Org. Lett. 1999, manuscript in preparation.
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98. Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769-1772.
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