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Synfacts 2005(0): 0043-0043
DOI: 10.1055/s-2005-869938
DOI: 10.1055/s-2005-869938
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Enantioselective [3+2] Cycloaddition of Allenylsilanes with α-Imino Esters
K. Daidouji, K. Fuchibe, T. Akiyama*
Gakushuin University, Japan
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
20. Juli 2005 (online)

Significance
The first enantioselective [3+2] cycloaddition reaction of 1-alkyl-substituted allenylsilanes with an α-imino ester is reported using a chiral Cu(I) catalyst. The presence of an α-alkyl group was essential for the reaction to succeed and a range of alkyl substituents was demonstrated. Use of a highly reactive aldimine is necessary to drive the reaction and only one example of an iminoester substrate gave the desired product. The vinyl silane functionality in the dehydroproline products allows further derivatization.