AI Article Synopsis
- The treatment of N-4,5-hexadienyl carbamate (2a) with a specific gold and silver catalyst at low temperatures yields high levels of 2-vinylpyrrolidine (3a) with impressive purity (97% yield) and enantiomeric excess (81% ee).
- This method demonstrates the effectiveness of gold(I)-catalyzed enantioselective hydroamination in synthesizing compounds with various carbamate groups.
- The process also shows compatibility with terminal disubstitution of the allenyl group, indicating its versatility in organic synthesis.
Article Abstract
Treatment of the N-4,5-hexadienyl carbamate 2a with a catalytic 1:2 mixture of [(S)-1]Au2Cl2 [(S)-1 = (S)-3,5-t-Bu-4-MeO-MeOBIPHEP] and AgClO4 in m-xylene at -40 degrees C for 24 h led to isolation of 2-vinylpyrrolidine 3a in 97% yield with 81% ee. Gold(I)-catalyzed enantioselective hydroamination was effective for a number of carbamate groups and tolerated terminal disubstitutution of the allenyl moiety.
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| http://dx.doi.org/10.1021/ol071108n | DOI Listing |
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