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Volumn 350, Issue 4, 2008, Pages 619-623

(Advanced Synthesis and Catalysis (2008) 4, (619-623) DOI 10.1002/adsc.200700504);Rationally-designed S-chiral bissulfinamides as highly enantioselective organocatalysts for reduction of ketimines

Author keywords

Asymmetric reduction; Ketimines; Organocatalysis; S chiral bissulfinamide

Indexed keywords


EID: 53849138558     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200890017     Document Type: Erratum
Times cited : (89)

References (45)
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    • For recent reviews, see: a) D. Morton, R. A. Stockman, Tetrahedron 2006, 62, 8869;
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    • Several S-chiral sulfoxides were previously reported to promote asymmetric allylations, which, however, were not catalytic and were all used in at least a stoichometric amount to achieve reasonable reactivity and stereoselectivity, see: a S. Kobayashi, C. Ogawa, H. Konishi, M. Sugiura, J. Am. Chem. Soc. 2003, 125, 6610;
    • Several S-chiral sulfoxides were previously reported to promote asymmetric allylations, which, however, were not catalytic and were all used in at least a stoichometric amount to achieve reasonable reactivity and stereoselectivity, see: a) S. Kobayashi, C. Ogawa, H. Konishi, M. Sugiura, J. Am. Chem. Soc. 2003, 125, 6610;
  • 15
    • 0034614084 scopus 로고    scopus 로고
    • A similar strategy has been previously adopted by Denmark's group for developing the bisphosphoramide catalyst system, see: a
    • A similar strategy has been previously adopted by Denmark's group for developing the bisphosphoramide catalyst system, see: a) S. E. Denmark, J. Fu, J. Am. Chem. Soc. 2000, 122, 12021;
    • (2000) J. Am. Chem. Soc , vol.122 , pp. 12021
    • Denmark, S.E.1    Fu, J.2
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    • For other types of chiral organocatalysts we previously developed for the asymmetric reduction of imines by HSiCl3, see: a Z. Wang, X. Ye, S. Wei, P. Wu, A. Zhang, J. Sun, Org. Lett. 2006, 8, 999;
    • 3, see: a) Z. Wang, X. Ye, S. Wei, P. Wu, A. Zhang, J. Sun, Org. Lett. 2006, 8, 999;
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    • For selected recent examples of highly enantioselective reduction of ketimines, see: a
    • For selected recent examples of highly enantioselective reduction of ketimines, see: a) Y. Wang, S. Lu, Y.-G. Zhou, J. Org. Chem. 2007, 72, 3729;
    • (2007) J. Org. Chem , vol.72 , pp. 3729
    • Wang, Y.1    Lu, S.2    Zhou, Y.-G.3
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    • This general procedure was found to be ineffective for the synthesis of 5c, for which a different multi-step synthetic procedure was developed see the Supporting Information
    • This general procedure was found to be ineffective for the synthesis of 5c, for which a different multi-step synthetic procedure was developed (see the Supporting Information).
  • 45
    • 53949109126 scopus 로고    scopus 로고
    • It should be noted that the present catalyst system is not effective for the reduction of the following two different types of keimines under the optimal conditions: Chemical Equation Presented
    • It should be noted that the present catalyst system is not effective for the reduction of the following two different types of keimines under the optimal conditions: (Chemical Equation Presented)


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