Gold-catalyzed intramolecular hydroamination of allenes: a case of chirality transfer |
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Authors: | Nitin T Patil |
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Institution: | Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan |
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Abstract: | The hydroamination of allenes proceeded smoothly in the presence of gold catalysts to give the corresponding 2-vinyl pyrrolidines and piperidines in high yields. The reaction is very efficient and can be carried out with only 1-5 mol % catalyst at room temperature and under extremely mild conditions. As an example of chirality transfer, it is shown that aminoallene 1a (96% ee), synthesized from (S)-(−)-1-octyn-3-ol, was converted into the corresponding pyrrolidine 2a (94% ee) in 99% yield. |
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Keywords: | Allene Gold catalyst Hydroamination Nitrogen heterocycles Chirality transfer |
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