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Volumn 74, Issue 6, 2009, Pages 2547-2553

Modular stereoeontrolled assembly of R2Zn, cyclic enones and N-tert-butanesulfinyl imines

Author keywords

[No Author keywords available]

Indexed keywords

BAEYER-VILLIGER OXIDATIONS; PHOSPHORAMIDITE LIGANDS; STEREOGENIC CENTERS;

EID: 64149099331     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802812w     Document Type: Article
Times cited : (37)

References (50)
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    • Recent discussions of asymmetric multicomponent reactions:(a) Marcaccini, S.; Torroba, T. In Multicomponent Reactions; Zhu, J., Bienayme, H., Eds.; Wiley-VCH: Wienheim, 2005; p 33.
    • Recent discussions of asymmetric multicomponent reactions:(a) Marcaccini, S.; Torroba, T. In Multicomponent Reactions; Zhu, J., Bienayme, H., Eds.; Wiley-VCH: Wienheim, 2005; p 33.
  • 6
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    • Tietze, L. F, Brasche, G, Gericke, K, Eds, Wiley-VCH: Weinheim
    • (f) Domino Reactions in Organic Synthesis; Tietze, L. F., Brasche, G., Gericke, K., Eds.; Wiley-VCH: Weinheim, 2006.
    • (2006) Domino Reactions in Organic Synthesis
  • 7
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    • Heathcock, C. H, Ed, Pergamon Press: Oxford, Chapter 4, p
    • Kleinman, E. F. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 4, p 893.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 893
    • Kleinman, E.F.1
  • 9
    • 0034553418 scopus 로고    scopus 로고
    • For leading references see:a
    • For leading references see:(a) Ishimaru, K.; Kojima, T. J. Org. Chem. 2000, 65, 8395.
    • (2000) J. Org. Chem , vol.65 , pp. 8395
    • Ishimaru, K.1    Kojima, T.2
  • 20
    • 33747113614 scopus 로고    scopus 로고
    • For a recent review see:a
    • For a recent review see:(a) Morton, D.; Stockman, R. A. Tetrahedron 2006, 62, 8869.
    • (2006) Tetrahedron , vol.62 , pp. 8869
    • Morton, D.1    Stockman, R.A.2
  • 26
    • 0034801512 scopus 로고    scopus 로고
    • For an isolated example where the three stereogenic centers are controled by the chiral ligand L1 see:(d) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2001, 123, 5841.
    • (c) For an isolated example where the three stereogenic centers are controled by the chiral ligand L1 see:(d) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2001, 123, 5841.
  • 27
    • 40949099010 scopus 로고    scopus 로고
    • A portion of these studies have been previously communicated, see:(a) González-Gómez, J. C.; Foubelo, F.; Yus, M. Tetrahedron Lett. 2008, 49, 2343.
    • A portion of these studies have been previously communicated, see:(a) González-Gómez, J. C.; Foubelo, F.; Yus, M. Tetrahedron Lett. 2008, 49, 2343.
  • 28
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    • Highlights
    • (b) Highlights: Synfacts 2008, 7. 0725.
    • (2008) Synfacts , vol.7 , pp. 0725
  • 31
    • 0033582571 scopus 로고    scopus 로고
    • N-tertButanesulfinyl imines are readily prepared from aldehydes and N-tertbutanesulfinamides (Ss and Rs are commercially available in >99% ee), following the procedure reported in: Liu, G.; Cogan, D. A.; Owens, T. D.; Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 1278.
    • N-tertButanesulfinyl imines are readily prepared from aldehydes and N-tertbutanesulfinamides (Ss and Rs are commercially available in >99% ee), following the procedure reported in: Liu, G.; Cogan, D. A.; Owens, T. D.; Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 1278.
  • 32
    • 0028813198 scopus 로고    scopus 로고
    • In the aziridination of sulfinimines it was recognized early that the replacement of the p-toluene motif with a tert-butyl group significantly increased the stereoinduction: García Ruano, J. L, Fernandez, I, Hamdouchi, C. Tetrahedron Lett. 1995, 36, 295
    • In the aziridination of sulfinimines it was recognized early that the replacement of the p-toluene motif with a tert-butyl group significantly increased the stereoinduction: García Ruano, J. L.; Fernandez, I.; Hamdouchi, C. Tetrahedron Lett. 1995, 36, 295.
  • 33
    • 0034800027 scopus 로고    scopus 로고
    • For an example where a chiral acetal overcome the directing induction of the chiral enolate in a tandem enantioselective conjugate addition-aldol reaction, see:(a) Alexakis, A, Trevitt, G. P, Bernardinelli, G. J. Am. Chem. Soc. 2001, 123, 4358
    • For an example where a chiral acetal overcome the directing induction of the chiral enolate in a tandem enantioselective conjugate addition-aldol reaction, see:(a) Alexakis, A.; Trevitt, G. P.; Bernardinelli, G. J. Am. Chem. Soc. 2001, 123, 4358.
  • 34
    • 34247582194 scopus 로고    scopus 로고
    • To the best of our knowledge, only a few examples of multicomponent reactions Mat include chiral sulfinimines have been recently reported:(a) Kamimura, A.; Okawa, H.; Morisaki, Y.; Ishikawa, S.; Uno, H. J. Org. Chem. 2007, 72, 3569.
    • To the best of our knowledge, only a few examples of multicomponent reactions Mat include chiral sulfinimines have been recently reported:(a) Kamimura, A.; Okawa, H.; Morisaki, Y.; Ishikawa, S.; Uno, H. J. Org. Chem. 2007, 72, 3569.
  • 37
    • 64149120867 scopus 로고    scopus 로고
    • The scope of the reaction was studied using 0.5 mmol of sulfinimines and 1.5 equiv of enone. However, compounds 3h and 3q were prepared using 1.2 equiv of enone, on a 2 mmol scale, observing similar isolated yields and stereoselectivities.
    • The scope of the reaction was studied using 0.5 mmol of sulfinimines and 1.5 equiv of enone. However, compounds 3h and 3q were prepared using 1.2 equiv of enone, on a 2 mmol scale, observing similar isolated yields and stereoselectivities.
  • 38
    • 4644252638 scopus 로고    scopus 로고
    • 2Zn conjugate addition to cyclohexenone using L1, see:(a) Peña, D.; López, F.; Harutyunyan, S.-R.; Minnaard, A. J.; Feringa, B. L. Chem. Commun. 2004, 1836.
    • 2Zn conjugate addition to cyclohexenone using L1, see:(a) Peña, D.; López, F.; Harutyunyan, S.-R.; Minnaard, A. J.; Feringa, B. L. Chem. Commun. 2004, 1836.
  • 40
    • 64149098186 scopus 로고    scopus 로고
    • Crystal data (excluding structure factors) deposited at the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 671456.
    • Crystal data (excluding structure factors) deposited at the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 671456.
  • 46
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    • For comparison with 1H NMR data of related aldol systems, see:(a) Kitamura, M.: Miki, T.: Nakano, K.; Novori, R. Bull. Chem. Soc. Jpn. 2000, 73, 999.
    • For comparison with 1H NMR data of related aldol systems, see:(a) Kitamura, M.: Miki, T.: Nakano, K.; Novori, R. Bull. Chem. Soc. Jpn. 2000, 73, 999.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.