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Volumn 21, Issue 24, 2010, Pages 2934-2943

Experimental and theoretical studies on Mannich-type reactions of chiral non-racemic N-(benzyloxyethyl) nitrones

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; KETENE DERIVATIVE; LITHIUM; MANNICH BASE; NITRONE;

EID: 78951469365     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.12.004     Document Type: Article
Times cited : (14)

References (103)
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    • For recent reviews illustrating the convenience of using chiral auxiliaries see: Y. Gnas, and F. Glorius Synthesis 2006 1899 1930
    • (2006) Synthesis , pp. 1899-1930
    • Gnas, Y.1    Glorius, F.2
  • 72
    • 0035961112 scopus 로고    scopus 로고
    • Aromatic aldimines have also showed a considerable lack of reactivity with lithium enolate 6. See: S. Saito, K. Hatanaka, and S. Yamamoto Tetrahedron 57 2001 875 887
    • (2001) Tetrahedron , vol.57 , pp. 875-887
    • Saito, S.1    Hatanaka, K.2    Yamamoto, S.3
  • 79
    • 78951475561 scopus 로고    scopus 로고
    • The assigned configurations are based by considering the R group as the second in priority after the nitrogen atom, which correlates with aminoacids 9 and ent-9
    • The assigned configurations are based by considering the R group as the second in priority after the nitrogen atom, which correlates with aminoacids 9 and ent-9.
  • 96
    • 33746653867 scopus 로고    scopus 로고
    • L.R. Domingo, M. Arno, P. Merino, and T. Tejero Eur. J. Org. Chem. 2006 3464 3472 There is another report on this reaction (see: Milet, A.; Gimbert, Y.; Greene, A. E. J. Comput. Chem. 2006, 27, 157-162). However, this report, carried out with very simple models far from actual reaction systems, did not consider the presence either Lewis acids or solvent, claiming a concerted mechanism. In our previous study we demonstrated (both theoretically and experimentally) that the reaction in the absence of any Lewis acid is not possible, a stepwise mechanism being much more favourable when a Lewis acid is present and solvent interactions are considered
    • (2006) Eur. J. Org. Chem. , pp. 3464-3472
    • Domingo, L.R.1    Arno, M.2    Merino, P.3    Tejero, T.4
  • 97
    • 78951478123 scopus 로고    scopus 로고
    • -1.
    • -1.
  • 98
    • 78951470705 scopus 로고    scopus 로고
    • It is also possible to consider rotation along the opposite pathway. However, this possibility was discarded because it led to the intermediate orthoester formed through TS3, which is not actually obtained. This route was clearly energetically unfavoured (see below).
    • It is also possible to consider rotation along the opposite pathway. However, this possibility was discarded because it led to the intermediate orthoester formed through TS3, which is not actually obtained. This route was clearly energetically unfavoured (see below).
  • 99
    • 78951493196 scopus 로고    scopus 로고
    • We have carried out the full theoretical study in the gas-phase, which is necessary for introducing solvation correction. These results as well as additional calculations considering introduction of diffuse functions and solvation effects for pathways corresponding to higher TSs, including the concerted pathway, are available from the authors on request. Diez-Martinez, A. Ph.D. Dissertation, in course.
    • We have carried out the full theoretical study in the gas-phase, which is necessary for introducing solvation correction. These results as well as additional calculations considering introduction of diffuse functions and solvation effects for pathways corresponding to higher TSs, including the concerted pathway, are available from the authors on request. Diez-Martinez, A. Ph.D. Dissertation, in course.
  • 100
    • 78951481514 scopus 로고    scopus 로고
    • 2 = Me, iPr) are available from the authors on request. Diez-Martinez, A. Ph.D. Dissertation, in course.
    • 2 = Me, iPr) are available from the authors on request. Diez-Martinez, A. Ph.D. Dissertation, in course.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.