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0002077493
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Asymmetric phase transfer reactions
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Ojima, I., Ed.; Wiley: New York
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(a) O'Donnell, M. J. Asymmetric Phase Transfer Reactions. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley: New York, 1993.
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Catalytic Asymmetric Synthesis
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O'Donnell, M.J.1
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(b) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414.
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(c) Corey, E. J.; Zhang, F.-Y. Angew. Chem., Int. Ed. 1999, 38, 1931.
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(f) Arai, S.; Shirai, Y.; Ishida, T.; Shioiri, T. Tetrahedron 1999, 55, 6375.
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Tetrahedron
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Arai, S.1
Shirai, Y.2
Ishida, T.3
Shioiri, T.4
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9
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84932119188
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The solvolysis of C9 halogenated quinine and quinidine has been studied in the last century before the advent of modern spectroscopic and separation techniques: (a) Rabe, P. Liebigs Ann. Chem. 1949, 561, 132-158. (b) Rabe, P. Chem. Ber. 1941, 74, 725-728.
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(1949)
Liebigs Ann. Chem.
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Rabe, P.1
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84987350438
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The solvolysis of C9 halogenated quinine and quinidine has been studied in the last century before the advent of modern spectroscopic and separation techniques: (a) Rabe, P. Liebigs Ann. Chem. 1949, 561, 132-158. (b) Rabe, P. Chem. Ber. 1941, 74, 725-728.
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(1941)
Chem. Ber.
, vol.74
, pp. 725-728
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Rabe, P.1
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11
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0037782469
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note
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Replacement of the vinyl group by hydrogen creates enantiomers. The term pseudo-enantiomer is used routinely for related pairs of Cinchona alkaloids, e.g. quinine and quinidine.
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0038459321
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note
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The solvolysis of C9 mesylated quinine and quinidine (6′-R = OMe instead of 6′-R = H) was faster than that of 1-OMs and 2-OMs (4-12 h vs 3-4 d for the cinch bases). Cage expansion was less developed (9% for quinine and 36% for quinidine in MeOH). In methanol the products with intact [2.2.2]azabicyclic cage were formed with epimerization at C9 (C9-nat:C9-epi ∼ 1:1). For C9 carbocations derived from quinine and quinidine an open classical cation rather than a nitrogen-bridged species becomes more favorable because of extended conjugation with the 6′-OMe donor ii ↔ iii.
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0038459320
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note
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2 the crude product was purified by column chromatography to furnish 4-OH (82%).
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15
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0038459319
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note
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The synthesis of parent 1-azabicyc]o[3.2.2]nonan-3-one (iv) has very recently been put forward as InnoCentive Challenge 260715, $70 000 USD. See www.innocentive.com.
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0038797051
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note
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1H NMR and NOESY.
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33751146774
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Review of kinetic enantioselective protonation of enolates: Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2566. See also: (b) Zimmerman, H. E.; Wang, P. Org. Lett. 2002, 4, 2593.
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(1996)
Angew. Chem., Int. Ed. Engl.
, vol.35
, pp. 2566
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Fehr, C.1
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0012144938
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Review of kinetic enantioselective protonation of enolates: Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2566. See also: (b) Zimmerman, H. E.; Wang, P. Org. Lett. 2002, 4, 2593.
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(2002)
Org. Lett.
, vol.4
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Zimmerman, H.E.1
Wang, P.2
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note
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The structure of the nitrogen-bridged intermediate remains open to discussion. While we prefer a flat-topped a-bridged species, a referee has suggested that the limiting case of the highly electrophilic, parent model cation (Q′= H and vinyl group replaced by H) in the gas phase can be described as a conventional aziridinium ion (B3LYP/6-31G* calculations).
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Cf. also reviews on structural studies of the 2-norbornyl cation: Olah, G. A.; Prakash, G. K. S.; Saunders, M. Acc. Chem. Res. 1983, 16, 440. (b) Methoden der Organischen Chemie, Houben-Weyl; Hanack, M., Ed.; Thieme: Stuttgart, Germany, 1990; Vol. E19c. (c) Saunders, M.; Jiménez-Vazquez, H. A. Chem. Rev. 1991, 91, 375. (d) X-ray crystal structures: Laube, T. Acc. Chem. Res. 1995, 28, 339. (e) Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, 3rd ed.; Plenum Press: New York, 1993.
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Acc. Chem. Res.
, vol.16
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Olah, G.A.1
Prakash, G.K.S.2
Saunders, M.3
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21
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0003695099
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Hanack, M., Ed.; Thieme: Stuttgart, Germany
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Cf. also reviews on structural studies of the 2-norbornyl cation: Olah, G. A.; Prakash, G. K. S.; Saunders, M. Acc. Chem. Res. 1983, 16, 440. (b) Methoden der Organischen Chemie, Houben-Weyl; Hanack, M., Ed.; Thieme: Stuttgart, Germany, 1990; Vol. E19c. (c) Saunders, M.; Jiménez-Vazquez, H. A. Chem. Rev. 1991, 91, 375. (d) X-ray crystal structures: Laube, T. Acc. Chem. Res. 1995, 28, 339. (e) Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, 3rd ed.; Plenum Press: New York, 1993.
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(1990)
Methoden der Organischen Chemie, Houben-Weyl
, vol.E19C
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22
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0002824973
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Cf. also reviews on structural studies of the 2-norbornyl cation: Olah, G. A.; Prakash, G. K. S.; Saunders, M. Acc. Chem. Res. 1983, 16, 440. (b) Methoden der Organischen Chemie, Houben-Weyl; Hanack, M., Ed.; Thieme: Stuttgart, Germany, 1990; Vol. E19c. (c) Saunders, M.; Jiménez-Vazquez, H. A. Chem. Rev. 1991, 91, 375. (d) X-ray crystal structures: Laube, T. Acc. Chem. Res. 1995, 28, 339. (e) Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, 3rd ed.; Plenum Press: New York, 1993.
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Chem. Rev.
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Saunders, M.1
Jiménez-Vazquez, H.A.2
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Cf. also reviews on structural studies of the 2-norbornyl cation: Olah, G. A.; Prakash, G. K. S.; Saunders, M. Acc. Chem. Res. 1983, 16, 440. (b) Methoden der Organischen Chemie, Houben-Weyl; Hanack, M., Ed.; Thieme: Stuttgart, Germany, 1990; Vol. E19c. (c) Saunders, M.; Jiménez-Vazquez, H. A. Chem. Rev. 1991, 91, 375. (d) X-ray crystal structures: Laube, T. Acc. Chem. Res. 1995, 28, 339. (e) Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, 3rd ed.; Plenum Press: New York, 1993.
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Acc. Chem. Res.
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Laube, T.1
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Plenum Press, New York
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Cf. also reviews on structural studies of the 2-norbornyl cation: Olah, G. A.; Prakash, G. K. S.; Saunders, M. Acc. Chem. Res. 1983, 16, 440. (b) Methoden der Organischen Chemie, Houben-Weyl; Hanack, M., Ed.; Thieme: Stuttgart, Germany, 1990; Vol. E19c. (c) Saunders, M.; Jiménez-Vazquez, H. A. Chem. Rev. 1991, 91, 375. (d) X-ray crystal structures: Laube, T. Acc. Chem. Res. 1995, 28, 339. (e) Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, 3rd ed.; Plenum Press: New York, 1993.
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(1993)
Advanced Organic Chemistry, 3rd Ed.
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Sundberg, R.J.2
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Org. Lett.
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(c) Braje, W. M.; Wartchow, R.; Hoffmann, H. M. R. Angew. Chem., Int. Ed. 1999, 38, 2540.
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