Gold-catalyzed bicyclic annulations of 4-methoxy-1,2-dienyl-5-ynes with isoxazoles to form indolizine derivatives via an Au-π-allene intermediate

Gold-catalyzed bicyclic annulations of 4-methoxy-1,2-dienyl-5-ynes with isoxazoles afford indolizine derivatives with a structural rearrangement. The mechanism of these new annulations does not involve α-imino gold carbenes generated from gold π-alkyne intermediates. We postulate alkyne attack on go...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2019-07, Vol.10 (26), p.6437-6442
Main Authors: Kulandai Raj, Antony Sekar, Tan, Kuo-Chen, Chen, Liang-Yu, Cheng, Mu-Jeng, Liu, Rai-Shung
Format: Article
Language:English
Subjects:
Alkynes
Allene
Carbenes
Chemistry
Crystallography
Derivatives
Gold
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Summary:Gold-catalyzed bicyclic annulations of 4-methoxy-1,2-dienyl-5-ynes with isoxazoles afford indolizine derivatives with a structural rearrangement. The mechanism of these new annulations does not involve α-imino gold carbenes generated from gold π-alkyne intermediates. We postulate alkyne attack on gold π-allenes, yielding vinyl gold carbenes. These newly generated carbenes react with isoxazole derivatives to yield Z-3-imino-2-en-1-als, further enabling sequential cyclizations to deliver indolizine derivatives in two distinct classes.
ISSN:2041-6520
2041-6539
DOI:10.1039/c9sc00735k