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Volumn 61, Issue 23, 1996, Pages 8002-8003

Enantioselectivity increases with reactivity: Electronically controlled asymmetric addition of diethylzinc to aromatic aldehydes catalyzed by a chiral pyridylphenol

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EID: 0001447903     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9609889     Document Type: Article
Times cited : (96)

References (29)
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    • For recent reviews, see: (a) Kotha, S. Tetrahedron 1994, 50, 3639. (b) Noyori, R. Ibid. 1994, 50, 4259. (c) Nugent, W. A.; RajanBabu, T. V.; Burk, M. J. Science 1993, 259, 479. (d) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833. (e) Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36. (f) Shibata, T.; Mirioka, M.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc. 1996, 118, 471.
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    • For recent reviews, see: (a) Kotha, S. Tetrahedron 1994, 50, 3639. (b) Noyori, R. Ibid. 1994, 50, 4259. (c) Nugent, W. A.; RajanBabu, T. V.; Burk, M. J. Science 1993, 259, 479. (d) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833. (e) Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36. (f) Shibata, T.; Mirioka, M.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc. 1996, 118, 471.
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    • For recent reviews, see: (a) Kotha, S. Tetrahedron 1994, 50, 3639. (b) Noyori, R. Ibid. 1994, 50, 4259. (c) Nugent, W. A.; RajanBabu, T. V.; Burk, M. J. Science 1993, 259, 479. (d) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833. (e) Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36. (f) Shibata, T.; Mirioka, M.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc. 1996, 118, 471.
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    • For recent reviews, see: (a) Kotha, S. Tetrahedron 1994, 50, 3639. (b) Noyori, R. Ibid. 1994, 50, 4259. (c) Nugent, W. A.; RajanBabu, T. V.; Burk, M. J. Science 1993, 259, 479. (d) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833. (e) Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36. (f) Shibata, T.; Mirioka, M.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc. 1996, 118, 471.
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    • note
    • R = 13.0 min, flow rate 0.3 mL/min, hexane/2-propanol = 4:1). The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 IEZ, UK.
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    • (a) IUPAC Tentative Rule for the Nomenclature of Organic Chemistry: J. Org. Chem, 1970, 35, 2849.
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    • note
    • Dagger; is the free energy difference between two diastereomeric transition states leading to enantiomeric products.


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