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For examples of asymmetric tandem catalytic enone conjugate addition/aldol trapping, see a) S. J. Taylor, M. O. Duffey, J. P. Morken, J. Am. Chem. Soc. 2000, 122, 4528-4529;
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For recent examples of catalytic enantioselective enone conjugate addition followed by enolate traping, see a) M. Kitama, T. Miki, K. Nakano, R. Noyori, Tetrahedron Lett. 1996, 37, 5141-5144;
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For a first example of the enantioselective protonation of a rhodium enolate intermediate (18% ee), see S. H. Bergens, B. Bosnich, J. Am. Chem. Soc. 1991, 113, 958-967.
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0000997168
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When we started our studies only one example was described of such a transformation in which the 1,4-addition of phenylboronic acid to methyl α-acetamidoacrylate catalyzed by a rhodium complex chelated with a binol-based diphosphonite chiral ligand furnished the phenylalanine derivative in 77% ee on protonation with water, but using excess NaF as an additive: M. T. Reetz, D. Moulin, A. Gosberg, Org. Lett. 2001, 3, 4083-4085.
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During the refereeing process a related reaction was published using aryl boronic acids as organometallic partners and water as the proton source with ee values ranging from 37 to 72%: C. J. Chapman, K. J. Wadsworth, C. G. Frost, J. Organomet. Chem. 2003, 680, 206-211.
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For a racemic version, see R. A. Batey, A. N. Thadani, D. V. Smil, Org. Lett. 1999, 1, 1683-1686; for asymmetric 1,4-additions, see M. Pucheault, S. Darses, J.-P. Genet, Tetrahedron Lett, 2002, 43, 6155-6157; M. Pucheault, S. Darses, J.-P. Genet, Eur J. Org. Chem. 2002, 3552-3557.
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For a racemic version, see R. A. Batey, A. N. Thadani, D. V. Smil, Org. Lett. 1999, 1, 1683-1686; for asymmetric 1,4-additions, see M. Pucheault, S. Darses, J.-P. Genet, Tetrahedron Lett, 2002, 43, 6155-6157; M. Pucheault, S. Darses, J.-P. Genet, Eur J. Org. Chem. 2002, 3552-3557.
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For a racemic version, see R. A. Batey, A. N. Thadani, D. V. Smil, Org. Lett. 1999, 1, 1683-1686; for asymmetric 1,4-additions, see M. Pucheault, S. Darses, J.-P. Genet, Tetrahedron Lett, 2002, 43, 6155-6157; M. Pucheault, S. Darses, J.-P. Genet, Eur J. Org. Chem. 2002, 3552-3557.
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Such complexes have been shown to be intermediates in 1,4-additions of organometallic reagents (particularly organoboronic acids) to enones: T. Hayashi, M. Takahashi, Y. Takaya, M. Ogasawara, J. Am. Chem. Soc. 2002, 124, 5052-5058.
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1042297550
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2, 10%), (R)-6,6′ -dimethoxy-2,2′-bis[di (3,5-di-tert-butylphenyl)-phosphanyl)-1,1′ -biphenyl ((R)-3,5-tBuMeOBiphep, 9%).
-
-
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50
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An inhibitory effect was observed upon the addition of acids in the rhodium-catalyzed 1,4-addition of organoboronic acids: S. Sakuma, N. Miyaura, J. Org. Chem. 2001, 66, 8944-8946.
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Ortho-substituted phenols that are capable of forming chelate complexes have been used successfully in the diastereoselective protonation of enolate intermediates: N. Krause, Angew. Chem. 1994, 106, 1845-1847; Angew. Chem. Int. Ed. Engl. 1994, 33, 1764-1765; review: N. Krause, S. Ebert, A. Haubrich, Liebigs Ann. 1997, 2409-2418.
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Krause, N.1
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52
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33749027108
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Ortho-substituted phenols that are capable of forming chelate complexes have been used successfully in the diastereoselective protonation of enolate intermediates: N. Krause, Angew. Chem. 1994, 106, 1845-1847; Angew. Chem. Int. Ed. Engl. 1994, 33, 1764-1765; review: N. Krause, S. Ebert, A. Haubrich, Liebigs Ann. 1997, 2409-2418.
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53
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33749005694
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Ortho-substituted phenols that are capable of forming chelate complexes have been used successfully in the diastereoselective protonation of enolate intermediates: N. Krause, Angew. Chem. 1994, 106, 1845-1847; Angew. Chem. Int. Ed. Engl. 1994, 33, 1764-1765; review: N. Krause, S. Ebert, A. Haubrich, Liebigs Ann. 1997, 2409-2418.
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For 1,4-additions of organosilanes catalyzed by rhodium(I) complexes, see a) S. Oi, M. Moro, Y. Inoue, Organometallics 2001, 20, 1036-1037;
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