Catalytic enantioselective conjugate addition with Grignard reagents

Accounts of Chemical Research

Volumn 40, Issue 3, 2007, Pages 179-188

  López, Fernando ^a,b   Minnaard, Adriaan J ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34147221694     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar0501976     Document Type: Article

References (70)

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28. For new recent examples, published after submission of this manuscript, see: (c) Martin, D.; Kehrli, S.; d'Augustin, M.; Clavier, H.; Mauduit, M.; Alexakis, A. Copper-Catalyzed Asymmetric Conjugate Addition of Grignard Reagents to Trisubstituted Enones. Construction of All-Carbon Quaternary Chiral Centers. J. Am. Chem. Soc. 2006, 128, 8416-8417.
29. (d) Howell, G. P.; Fletcher, S. P.; Geurts, K.; ter Horst, B.; Feringa, B. L., Catalytic Asymmetric Synthesis of Acyclic Arrays by Tandem 1,4-Addition-Aldol Reactions. J. Am. Chem. Soc. 2006, 128, 14977-14985.
30. (a) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. Rhodium-Catalyzed Asymmetric 1,4-Addition of Aryl and Alkenylboronic Acids to Enones. J. Am. Chem. Soc. 1998, 120, 5579-5580.
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33. (d) Boiteau, J. G.; Minnaard, A. J.; Feringa, B. L. High efficiency and enantioselectivity in the Rh-catalyzed conjugate addition of arylboronic acids using monodentate phosphoramidites, J. Org. Chem., 2003, 68, 9481-9484.
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35. (a) Knotter, D. M.; Grove, D. M.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. A New Class of Organocopper and Organocuprate Compounds Derived from Copper(I) Arenethiolates. J. Am. Chem. Soc. 1992, 114, 3400-3410.
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44. López, F.; Harutyunyan, S. R.; Minnaard, A. J.; Feringa, B. L. Copper-catalyzed Enantioselective Conjugate Addition of Grignard Reagents to Acyclic Enones J. Am. Chem. Soc. 2004, 126, 12784-12785.
45. For selected examples, see: (a) Mizutani, H.; Degrado, S. J., Hoveyda, A. H. Cu-catalyzed Asymmetric Conjugate Additions of Alkylzinc Reagents to Acyclic Aliphatic Enones. J. Am. Chem. Soc. 2002, 124, 779-781.
46. (b) Lipshutz, B. H.; Servesko, J. M. CuH-catalyzed Asymmetric Conjugate Reductions of Acyclic Enones. Angew. Chem., Int. Ed. 2003, 42, 4789-4792.
47. (c) Hayashi, T.; Ueyama, K.; Tokunaga, N.; Yoshida, K. A Chiral Chelating Diene as a New Type of Chiral Ligand for Transition Metal Catalysts: Its Preparation and Use for the Rhodium-catalyzed Asymmetric 1,4-Addition. J. Am. Chem. Soc. 2003, 125, 11508-11509.
48. 3 to Linear Aliphatic Enones by a Designed Catalyst. Chem. Eur. J. 2003, 9, 776-783.
49. (f) See also refs 18a, 19, and 21.
50. With 1 mol % catalyst, the products were obtained with equal enantioselectivity and slightly lower regioselectivity.
51. For a Rh-catalyzed asymmetric CA of arylboronic reagents to α,β-unsaturated esters, see: Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura N. Asymmetric Conjugate 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Esters Catalyzed by Rhodium(I)/(S)-Binap. J. Org. Chem. 2000, 65, 5951-5955 and references therein.
52. Hird, A. W.; Hoveyda, A. H. Cu-catalyzed Enantioselective Conjugate Additions of Alkylzinc Reagents to Unsaturated N-Acyloxazolidinones Promoted by a Chiral Triamide Phosphane. Angew. Chem., Int. Ed. 2003, 42, 1276-1279.
53. For an alternative strategy, see: Schuppan, J.; Minnaard, A. J.; Feringa, B. L. A Catalytic and Iterative Route to β-Substituted Esters via Highly Enantioselective Conjugate Addition of Dimethylzincto Unsaturated Malonates. Chem. Commun. 2004, 792-793.
54. López, F.; Harutyunyan, S. R.; Meetsma, A.; Minnaard, A. J.; Feringa, B. L. Copper-catalyzed Enantioselective Conjugate Addition of Grignard Reagents to α,β-Unsaturated Esters. Angew. Chem., Int. Ed. 2005, 44, 2752-2756.
55. Harutyunyan, S. R.; López, F.; Browne, W. R.; Correa, A.; Peńa, D.; Badorrey, R.; Meetsma, A.; Minnaard, A. J.; Feringa, B. L. On the Mechanism of the Copper-Catalyzed Enantioselective 1,4-Addition of Grignard Reagents to α,β-Unsaturated Carbonyl Compounds. J. Am. Chem. Soc. 2006, 128, 9103-9118.
56. The reduced electron derealization in the thioester moiety, compared to oxoesters, results in a higher reactivity towards CA reactions. See ref 37.
57. Des Mazery, R.; Pullez, M.; López, F.; Harutyunyan, S. R.; Minnaard, A. J.; Feringa, B. L. An Iterative Catalytic Route to Enantiopure Deoxypropionate Subunits: Asymmetric Conjugate Addition of Grignard Reagents to α,β-Unsaturated Thioesters. J. Am. Chem. Soc. 2005, 127, 9966-9967.
58. The occurrence of polydeoxypropionate chains in numerous biologically relevant compounds and the paucity of iterative catalytic asymmetric procedures is a stimulus for the development of new methodologies.
59. For alternative iterative approaches, see: Novak, T.; Tan, Z.; Liang, B.; Negishi, E. All-catalytic, Efficient, and Asymmetric Synthesis of α,γ-Diheterofunctional Reduced Polypropionates via "One-pot" Zr-catalyzed Asymmetric Carboalumination-Pd-catalyzed Cross-coupling Tandem Process. J. Am. Chem. Soc. 2005, 127, 2838-2839 and references therein.
60. Nakamura, E.; Mori, S. Wherefore Are Thou Copper? Structures and Reaction Mechanisms of Organocuprate Clusters in Organic Chemistry. Angew. Chem., Int. Ed. 2000, 39, 3751-3771.
61. Woodward, S. Organocopper for the Craftsman Cunning at His Trade. Angew. Chem., Int. Ed. 2005, 44, 5560-5562.
62. (a) Yamanaka, M.; Kato, S.; Nakamura, E. Mechanism and Regioselectivity of Reductive Elimination of π-Allylcopper(III) Intermediates. J. Am. Chem. Soc, 2004, 126, 6287-6293.
63. (b) See also ref 40.
64. For selected reviews describing the progress in the field, see (c) Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2005, 44, 4435-4439.
65. (d) Alexakis, A.; Malan, C.; Lea, L; Tissot-Croset, K.; Polet, D.; Falciola, C. Chimia 2006, 60, 124-130.
66. (e) See also ref 17.
67. López, F.; van Zijl, A, W.; Minnaard, A. J.; Feringa, B. L. Highly Enantioselective Cu-catalysed Allylic Substitutions with Grignard Reagents. Chem. Commun. 2006, 409-411 and references cited therein.
68. (a) For a previous related example where high ee's were achieved with aromatic and cyclic aliphatic allylic substrates, see: Tissot-Croset, K.; Polet, D.; Alexakis, A. A. Highly Effective Phosphoramidite Ligand for Asymmetric Allylic Substitution Angew. Chem., Int. Ed. 2004, 43, 2426-2428.
69. N2 Reaction. Angew. Chem. Int. Ed. 2006, 45, 5995-5998.
70. (c) Geurts, K.; Fletcher, S. P.; Feringa, B. L. Copper Catalyzed Asymmetric Synthesis of Chiral Allylic Esters. J. Am. Chem. Soc. 2006, ASAP Article; DOI: 10.1021/ja065780b.