Origin of the diastereofacial selectivity in the nucleophilic addition to chiral acyclic ketones. An ab initio MO study

New Journal of Chemistry

Volumn 28, Issue 3, 2004, Pages 355-360

  Takahashi, Osamu ^a   Saito, Ko ^a   Kohno, Yuji ^b   Suezawa, Hiroko ^c   Ishihara, Shinji ^c   Nishio, Motohiro ^d  

^a HIROSHIMA UNIVERSITY   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

^c YOKOHAMA NATIONAL UNIVERSITY   (Japan)

^d CHPI Institute   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 PHENYLETHYL KETONE; ALCOHOL; BENCYCLANE; CARBON; KETONE DERIVATIVE; METHYL GROUP; OXYGEN; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CONFORMATION; DIASTEREOISOMER; ENERGY; GEOMETRY; HYDROGEN BOND; MATHEMATICAL MODEL; PRIORITY JOURNAL;

EID: 1642386988     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/b310173h     Document Type: Article

References (50)

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47. For criticisms to the secondary orbital interaction in stereoselectivity, see: J. I. Garcia, J. A. Majorai and L. Salvatella, Acc. Chem. Res., 2000, 33, 658-664; M. Sodupe, R. Rios, V. Branchadell, T. Nicholas, A. Oliva and J. J. Dannenberg, J. Am. Chem. Soc., 1997, 119, 4232-4238; B. W. Gung, Chem. Rev., 1999, 99, 1377-1386; G. Ujaque, P. S. Lee, K. N. Houk, M. F. Hentemann and S. J. Danishefsky, Chem.-Eur. J., 2002, 8, 3423-3430.
48. For criticisms to the secondary orbital interaction in stereoselectivity, see: J. I. Garcia, J. A. Majorai and L. Salvatella, Acc. Chem. Res., 2000, 33, 658-664; M. Sodupe, R. Rios, V. Branchadell, T. Nicholas, A. Oliva and J. J. Dannenberg, J. Am. Chem. Soc., 1997, 119, 4232-4238; B. W. Gung, Chem. Rev., 1999, 99, 1377-1386; G. Ujaque, P. S. Lee, K. N. Houk, M. F. Hentemann and S. J. Danishefsky, Chem.-Eur. J., 2002, 8, 3423-3430.
49. For criticisms to the secondary orbital interaction in stereoselectivity, see: J. I. Garcia, J. A. Majorai and L. Salvatella, Acc. Chem. Res., 2000, 33, 658-664; M. Sodupe, R. Rios, V. Branchadell, T. Nicholas, A. Oliva and J. J. Dannenberg, J. Am. Chem. Soc., 1997, 119, 4232-4238; B. W. Gung, Chem. Rev., 1999, 99, 1377-1386; G. Ujaque, P. S. Lee, K. N. Houk, M. F. Hentemann and S. J. Danishefsky, Chem.-Eur. J., 2002, 8, 3423-3430.
50. -1, respectively, at the MP2/6-311G(d,p)//MP2/6-31G(d), MP2/6-311G(d,p)//MP2/6-311G(d,p) and MP4/6-311G(d,p)//MP2/6-31G(d) levels of approximation. Note that the above values are the difference in the potential energy barrier and not the Gibbs energy difference as reported in Table 6. See also ref. 17.