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Synfacts 2005(2): 0258-0258
DOI: 10.1055/s-2005-916112
DOI: 10.1055/s-2005-916112
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York
Enantioselective Organocatalytic Michael Additions of Aldehydes to Enones
T. J. Peelen, Y. Chi, S. H. Gellman*
University of Wisconsin, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
25. Oktober 2005 (online)
Significance
The authors report that the addition of an appropriate achiral cocatalyst is important for the regioselectivity (Michael versus aldol additions) in the described reaction. Various cocatalysts with hydrogen bond donors were tested and those with adjacent hydrogen bond donors (i.e. catechol derivatives) provided the best results. NMR experiments showed that the imidazolidinone catalyst likely produced an enamine with E configuration, which was preformed and a competent nucleophile in the Michael addition.