Asymmetric organocatalysis of structurally well-defined chiral quaternary ammonium fluorides

Accounts of Chemical Research

Volumn 37, Issue 8, 2004, Pages 526-533

  Ooi, Takashi ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CINCHONA ALKALOID; FLUORIDE; QUATERNARY AMMONIUM DERIVATIVE; RESIN;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHIRALITY; ENANTIOSELECTIVITY; ION EXCHANGE; STEREOCHEMISTRY; SYNTHESIS; WETTABILITY;

EID: 4143054678     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar030060k     Document Type: Article

References (43)

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36. For rare examples of catalytic asymmetric Michael addition to α,β-unsaturated aldehydes, see: Yamaguchi, M.; Shiraishi, T.; Hirama, M. A Catalytic Enantioselective Michael Addition of a Simple Malonate to Prochiral α,Ø-Unsaturated Ketones and Aldehydes. Angew. Chem., Int. Ed. Engl. 1993, 32, 1176-1178. Yamaguchi, M.; Shiraishi, T.; Hirama, M. Asymmetric Michael Addition of Malonate Anions to Prochiral Acceptors Catalyzed by L-Proline Rubidium Salt. J. Org. Chem. 1996, 61, 3520-3530. Saito, M.; Nakajima, M.; Hashimoto, S. Enantioselective Conjugate Addition of Thiols to Enones and Enals Catalyzed by Chiral N-Oxide-Cadmium Complex. Chem. Commun. 2000, 1851-1852. Saito, M.; M.; Hashimoto, S. Enantioselective Conjugate Addition of Thiols to Cyclic Enones and Enals Catalyzed by Chiral N, N′-Dioxide-Cadmium Iodide Complex. Tetrahedron 2000, 56, 9589-9594. Kumaraswamy, G.; Sastry, M. N. V.; Jena, N. Calcium-BINOL: A Novel and Efficient Catalyst for Asymmetric Michael Reactions. Tetrahedron Lett. 2001, 42, 8515-8517. Paras, N. A.; MacMillan, D. W. C. The Enantioselective Organocatalytic 1,4-Addition of Electron-Rich Benzenes to α,β- Unsaturated Aldehydes. J. Am. Chem. Soc. 2002, 124, 7894-7895. Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. The First Enantioselective Organocatalytic Mukaiyama-Michael Reaction: A Direct Method for the Synthesis of Enantioenriched γ-Butenolide Architecture. J. Am. Chem. Soc. 2003, 125, 1192-1194.
37. For rare examples of catalytic asymmetric Michael addition to α,β-unsaturated aldehydes, see: Yamaguchi, M.; Shiraishi, T.; Hirama, M. A Catalytic Enantioselective Michael Addition of a Simple Malonate to Prochiral α,Ø-Unsaturated Ketones and Aldehydes. Angew. Chem., Int. Ed. Engl. 1993, 32, 1176-1178. Yamaguchi, M.; Shiraishi, T.; Hirama, M. Asymmetric Michael Addition of Malonate Anions to Prochiral Acceptors Catalyzed by L-Proline Rubidium Salt. J. Org. Chem. 1996, 61, 3520-3530. Saito, M.; Nakajima, M.; Hashimoto, S. Enantioselective Conjugate Addition of Thiols to Enones and Enals Catalyzed by Chiral N-Oxide-Cadmium Complex. Chem. Commun. 2000, 1851-1852. Saito, M.; M.; Hashimoto, S. Enantioselective Conjugate Addition of Thiols to Cyclic Enones and Enals Catalyzed by Chiral N, N′-Dioxide-Cadmium Iodide Complex. Tetrahedron 2000, 56, 9589-9594. Kumaraswamy, G.; Sastry, M. N. V.; Jena, N. Calcium-BINOL: A Novel and Efficient Catalyst for Asymmetric Michael Reactions. Tetrahedron Lett. 2001, 42, 8515-8517. Paras, N. A.; MacMillan, D. W. C. The Enantioselective Organocatalytic 1,4-Addition of Electron-Rich Benzenes to α,β- Unsaturated Aldehydes. J. Am. Chem. Soc. 2002, 124, 7894-7895. Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. The First Enantioselective Organocatalytic Mukaiyama-Michael Reaction: A Direct Method for the Synthesis of Enantioenriched γ-Butenolide Architecture. J. Am. Chem. Soc. 2003, 125, 1192-1194.
38. For rare examples of catalytic asymmetric Michael addition to α,β-unsaturated aldehydes, see: Yamaguchi, M.; Shiraishi, T.; Hirama, M. A Catalytic Enantioselective Michael Addition of a Simple Malonate to Prochiral α,Ø-Unsaturated Ketones and Aldehydes. Angew. Chem., Int. Ed. Engl. 1993, 32, 1176-1178. Yamaguchi, M.; Shiraishi, T.; Hirama, M. Asymmetric Michael Addition of Malonate Anions to Prochiral Acceptors Catalyzed by L-Proline Rubidium Salt. J. Org. Chem. 1996, 61, 3520-3530. Saito, M.; Nakajima, M.; Hashimoto, S. Enantioselective Conjugate Addition of Thiols to Enones and Enals Catalyzed by Chiral N-Oxide-Cadmium Complex. Chem. Commun. 2000, 1851-1852. Saito, M.; M.; Hashimoto, S. Enantioselective Conjugate Addition of Thiols to Cyclic Enones and Enals Catalyzed by Chiral N, N′-Dioxide-Cadmium Iodide Complex. Tetrahedron 2000, 56, 9589-9594. Kumaraswamy, G.; Sastry, M. N. V.; Jena, N. Calcium-BINOL: A Novel and Efficient Catalyst for Asymmetric Michael Reactions. Tetrahedron Lett. 2001, 42, 8515-8517. Paras, N. A.; MacMillan, D. W. C. The Enantioselective Organocatalytic 1,4-Addition of Electron-Rich Benzenes to α,β- Unsaturated Aldehydes. J. Am. Chem. Soc. 2002, 124, 7894-7895. Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. The First Enantioselective Organocatalytic Mukaiyama-Michael Reaction: A Direct Method for the Synthesis of Enantioenriched γ-Butenolide Architecture. J. Am. Chem. Soc. 2003, 125, 1192-1194.
39. For rare examples of catalytic asymmetric Michael addition to α,β-unsaturated aldehydes, see: Yamaguchi, M.; Shiraishi, T.; Hirama, M. A Catalytic Enantioselective Michael Addition of a Simple Malonate to Prochiral α,Ø-Unsaturated Ketones and Aldehydes. Angew. Chem., Int. Ed. Engl. 1993, 32, 1176-1178. Yamaguchi, M.; Shiraishi, T.; Hirama, M. Asymmetric Michael Addition of Malonate Anions to Prochiral Acceptors Catalyzed by L-Proline Rubidium Salt. J. Org. Chem. 1996, 61, 3520-3530. Saito, M.; Nakajima, M.; Hashimoto, S. Enantioselective Conjugate Addition of Thiols to Enones and Enals Catalyzed by Chiral N-Oxide-Cadmium Complex. Chem. Commun. 2000, 1851-1852. Saito, M.; M.; Hashimoto, S. Enantioselective Conjugate Addition of Thiols to Cyclic Enones and Enals Catalyzed by Chiral N, N′-Dioxide-Cadmium Iodide Complex. Tetrahedron 2000, 56, 9589-9594. Kumaraswamy, G.; Sastry, M. N. V.; Jena, N. Calcium-BINOL: A Novel and Efficient Catalyst for Asymmetric Michael Reactions. Tetrahedron Lett. 2001, 42, 8515-8517. Paras, N. A.; MacMillan, D. W. C. The Enantioselective Organocatalytic 1,4-Addition of Electron-Rich Benzenes to α,β- Unsaturated Aldehydes. J. Am. Chem. Soc. 2002, 124, 7894-7895. Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. The First Enantioselective Organocatalytic Mukaiyama-Michael Reaction: A Direct Method for the Synthesis of Enantioenriched γ-Butenolide Architecture. J. Am. Chem. Soc. 2003, 125, 1192-1194.
40. For rare examples of catalytic asymmetric Michael addition to α,β-unsaturated aldehydes, see: Yamaguchi, M.; Shiraishi, T.; Hirama, M. A Catalytic Enantioselective Michael Addition of a Simple Malonate to Prochiral α,Ø-Unsaturated Ketones and Aldehydes. Angew. Chem., Int. Ed. Engl. 1993, 32, 1176-1178. Yamaguchi, M.; Shiraishi, T.; Hirama, M. Asymmetric Michael Addition of Malonate Anions to Prochiral Acceptors Catalyzed by L-Proline Rubidium Salt. J. Org. Chem. 1996, 61, 3520-3530. Saito, M.; Nakajima, M.; Hashimoto, S. Enantioselective Conjugate Addition of Thiols to Enones and Enals Catalyzed by Chiral N-Oxide-Cadmium Complex. Chem. Commun. 2000, 1851-1852. Saito, M.; M.; Hashimoto, S. Enantioselective Conjugate Addition of Thiols to Cyclic Enones and Enals Catalyzed by Chiral N, N′-Dioxide-Cadmium Iodide Complex. Tetrahedron 2000, 56, 9589-9594. Kumaraswamy, G.; Sastry, M. N. V.; Jena, N. Calcium-BINOL: A Novel and Efficient Catalyst for Asymmetric Michael Reactions. Tetrahedron Lett. 2001, 42, 8515-8517. Paras, N. A.; MacMillan, D. W. C. The Enantioselective Organocatalytic 1,4-Addition of Electron-Rich Benzenes to α,β- Unsaturated Aldehydes. J. Am. Chem. Soc. 2002, 124, 7894-7895. Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. The First Enantioselective Organocatalytic Mukaiyama-Michael Reaction: A Direct Method for the Synthesis of Enantioenriched γ-Butenolide Architecture. J. Am. Chem. Soc. 2003, 125, 1192-1194.
41. For rare examples of catalytic asymmetric Michael addition to α,β-unsaturated aldehydes, see: Yamaguchi, M.; Shiraishi, T.; Hirama, M. A Catalytic Enantioselective Michael Addition of a Simple Malonate to Prochiral α,Ø-Unsaturated Ketones and Aldehydes. Angew. Chem., Int. Ed. Engl. 1993, 32, 1176-1178. Yamaguchi, M.; Shiraishi, T.; Hirama, M. Asymmetric Michael Addition of Malonate Anions to Prochiral Acceptors Catalyzed by L-Proline Rubidium Salt. J. Org. Chem. 1996, 61, 3520-3530. Saito, M.; Nakajima, M.; Hashimoto, S. Enantioselective Conjugate Addition of Thiols to Enones and Enals Catalyzed by Chiral N-Oxide-Cadmium Complex. Chem. Commun. 2000, 1851-1852. Saito, M.; M.; Hashimoto, S. Enantioselective Conjugate Addition of Thiols to Cyclic Enones and Enals Catalyzed by Chiral N, N′-Dioxide-Cadmium Iodide Complex. Tetrahedron 2000, 56, 9589-9594. Kumaraswamy, G.; Sastry, M. N. V.; Jena, N. Calcium-BINOL: A Novel and Efficient Catalyst for Asymmetric Michael Reactions. Tetrahedron Lett. 2001, 42, 8515-8517. Paras, N. A.; MacMillan, D. W. C. The Enantioselective Organocatalytic 1,4-Addition of Electron-Rich Benzenes to α,β- Unsaturated Aldehydes. J. Am. Chem. Soc. 2002, 124, 7894-7895. Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. The First Enantioselective Organocatalytic Mukaiyama-Michael Reaction: A Direct Method for the Synthesis of Enantioenriched γ-Butenolide Architecture. J. Am. Chem. Soc. 2003, 125, 1192-1194.
42. Ooi, T.; Doda, K.; Maruoka, K. Highly Enantioselective Michael Addition of Silyl Nitronates to α,β-Unsaturated Aldehydes Catalyzed by Designer Chiral Ammonium Bifluorides: Efficient Access to Optically Active γ-Nitro Aldehydes and Their Enol Silyl Ethers. J. Am. Chem. Soc. 2003, 125, 9022-9023. Ooi, T.; Morimoto, K.; Doda, K.; Maruoka, K. Evaluation of the Relationship between the Catalyst Structure and Regio- as well as Stereoselectivity in the Chiral Ammonium Bifluoride-Catalyzed Asymmetric Addition of Silyl Nitronates to α,β-Unsaturated Aldehydes. Chem. Lett. 2004, 33, 824-825.
43. Ooi, T.; Doda, K.; Maruoka, K. Highly Enantioselective Michael Addition of Silyl Nitronates to α,β-Unsaturated Aldehydes Catalyzed by Designer Chiral Ammonium Bifluorides: Efficient Access to Optically Active γ-Nitro Aldehydes and Their Enol Silyl Ethers. J. Am. Chem. Soc. 2003, 125, 9022-9023. Ooi, T.; Morimoto, K.; Doda, K.; Maruoka, K. Evaluation of the Relationship between the Catalyst Structure and Regio- as well as Stereoselectivity in the Chiral Ammonium Bifluoride-Catalyzed Asymmetric Addition of Silyl Nitronates to α,β-Unsaturated Aldehydes. Chem. Lett. 2004, 33, 824-825.