Stereoselection at the steady state by stereoconvergent reaction topography

Journal of the American Chemical Society

Volumn 120, Issue 2, 1998, Pages 329-341

  DeMello, Nicholas C ^a   Curran, Dennis P ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG;

ARTICLE; COMPUTER SIMULATION; CONTROLLED STUDY; KINETICS; NONHUMAN; STEADY STATE; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0032554014     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9724093     Document Type: Article

References (33)

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5. Treatises and books: (a) Izumi, Y.; Tai, A. Stereo-Differentiating Reactions; Academic Press: Japan, 1977; p 82. (b) Nógrádi, M. Stereoselective Synthesis; VCH: New York, 1996. (c) Houben-Weyl Methods of Organic Chemistry; Vol. E 21a, Stereoselective Synthesis; Helmchen, G., Ed.; Georg Thieme Verlag: Stuttgart, Germany, 1995. (d) Seyden-Penne, J. Chiral Auxilaries and Ligands in Asymmetric Synthesis; Wiley: New York, 1995.
6. Treatises and books: (a) Izumi, Y.; Tai, A. Stereo-Differentiating Reactions; Academic Press: Japan, 1977; p 82. (b) Nógrádi, M. Stereoselective Synthesis; VCH: New York, 1996. (c) Houben-Weyl Methods of Organic Chemistry; Vol. E 21a, Stereoselective Synthesis; Helmchen, G., Ed.; Georg Thieme Verlag: Stuttgart, Germany, 1995. (d) Seyden-Penne, J. Chiral Auxilaries and Ligands in Asymmetric Synthesis; Wiley: New York, 1995.
7. Treatises and books: (a) Izumi, Y.; Tai, A. Stereo-Differentiating Reactions; Academic Press: Japan, 1977; p 82. (b) Nógrádi, M. Stereoselective Synthesis; VCH: New York, 1996. (c) Houben-Weyl Methods of Organic Chemistry; Vol. E 21a, Stereoselective Synthesis; Helmchen, G., Ed.; Georg Thieme Verlag: Stuttgart, Germany, 1995. (d) Seyden-Penne, J. Chiral Auxilaries and Ligands in Asymmetric Synthesis; Wiley: New York, 1995.
8. (a) See: Curran, D. P.; Lin, C. H.; Qi, H.; Junggebauer, J. J. Am. Chem. Soc. 1998, 120, 342.
9. See also: (b) Curran, D. P.; Qi, H. Y.; DeMello, N. C.; Lin, C. H. J. Am. Chem. Soc. 1994, 776, 8430. (c) Curran, D. P.; Qi, H. Y. Helv. Chim. Acta 1996, 79, 21.
10. See also: (b) Curran, D. P.; Qi, H. Y.; DeMello, N. C.; Lin, C. H. J. Am. Chem. Soc. 1994, 776, 8430. (c) Curran, D. P.; Qi, H. Y. Helv. Chim. Acta 1996, 79, 21.
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16. More generally, the intermediates are diastereomeric, so the event does not have to be stereodivergent, it simply has to be divergent. Processes such as this can in principle deplete the minor stereoisomer by providing lower energy pathways to regioisomers or even completely different products.
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25. Elegant stereoconvergent strategies that rely on diastereomer formation with chemical, not physical separation have been introduced for resolutions of racemic mixtures. These all rely on selections at the first stage of the process. In general, a pair of enantiomers is selectively converted into two different diastereomers that are then processed with parallel reactions to the same product. See: Harada, T.; Shintani, T.; Oku, A. J. Am. Chem. Soc. 1995, 117, 144. Davis, A. P. Angew. Chem., Int. Ed. Engl. 1997, 36, 591.
26. Elegant stereoconvergent strategies that rely on diastereomer formation with chemical, not physical separation have been introduced for resolutions of racemic mixtures. These all rely on selections at the first stage of the process. In general, a pair of enantiomers is selectively converted into two different diastereomers that are then processed with parallel reactions to the same product. See: Harada, T.; Shintani, T.; Oku, A. J. Am. Chem. Soc. 1995, 117, 144. Davis, A. P. Angew. Chem., Int. Ed. Engl. 1997, 36, 591.
27. (l6) The second transformation may also be selective. If so, the four rates of reaction must be such that one stereoisomeric intermediate prefers one transformation, and the other radical shows a preference for the second transformation.
28. In fact, these achiral products are formed through convergences of their own, which are superimposed until the last step on the other convergences. In this respect, the "leakage" in Figure 8 is an artifact of representing the reaction topography in two dimensions.
29. For intramolecular reactions of silicon hydrides, see: Curran, D. P.; Xu, J. Y.; Lazzarini, E. J. Chem. Soc., Perkin Trans, I 1995, 3049.
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