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b) H. Danda, H. Nishikawa, K. Otaka, J. Org. Chem. 1991, 56, 6740.
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0037028924
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A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842.
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18
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33846519040
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We cannot preclude that the product may have played a role during its formation in the presence of proline as well
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We cannot preclude that the product may have played a role during its formation in the presence of proline as well.
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19
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33846518482
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To assess the effect of asymmetric induction, we have also included the reduced ee values of the product (eep) after deduction of the effect of the initial catalyst on the ee values of the isolated product: eep, n1/(n1-no))·eep′, no·eeo//n1, with eeo, ee value of the initially added product catalyst, eep′, observed ee value of isolated product, no, product initially added [mol, n1, total isolated product [mol
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1 = total isolated product [mol].
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20
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33846471319
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2 and toluene as solvents. While the reaction in toluene gave only traces of product, the yield in methylene chloride was 4-6 % with an ee value of the isolated product close to that of the initially added product (98 % ee).
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2 and toluene as solvents. While the reaction in toluene gave only traces of product, the yield in methylene chloride was 4-6 % with an ee value of the isolated product close to that of the initially added product (98 % ee).
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21
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33846473301
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Traces of p-methoxyaniline have been detected after workup. Unused starting material could be retrieved in all experiments, that is, the reaction does not proceed to completion.
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Traces of p-methoxyaniline have been detected after workup. Unused starting material could be retrieved in all experiments, that is, the reaction does not proceed to completion.
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22
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33846553250
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After keeping the product 3 for one month at -21°C, we observed a decrease in enantiomeric purity from 98 % ee to 53 % ee. However, no loss of enantiomeric purity was observed after 4 days at room temperature.
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After keeping the product 3 for one month at -21°C, we observed a decrease in enantiomeric purity from 98 % ee to 53 % ee. However, no loss of enantiomeric purity was observed after 4 days at room temperature.
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23
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0034750244
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For reviews on asymmetric aminocatalysis, see: a
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For reviews on asymmetric aminocatalysis, see: a) B. List, Synlett 2001, 1675;
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(2001)
Synlett
, pp. 1675
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List, B.1
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25
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33846489224
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+ may indicate the formation of a product-substrate complex.
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+ may indicate the formation of a product-substrate complex.
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26
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33846486994
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Gaussian03, Revision A.11.4, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, N. Rega, P. Salvador, J. J. Dannenberg, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc, Pittsburgh PA, 2002
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Gaussian03, Revision A.11.4, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, N. Rega, P. Salvador, J. J. Dannenberg, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburgh PA, 2002.
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