Unknown

Dataset Information

0

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


ABSTRACT: 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 ?-imino gold carbenes generated from gold ?-alkyne intermediates. We postulate alkyne attack on gold ?-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.

SUBMITTER: Kulandai Raj AS 

PROVIDER: S-EPMC6610539 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature

altmetric image

Publications

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

Kulandai Raj Antony Sekar AS   Tan Kuo-Chen KC   Chen Liang-Yu LY   Cheng Mu-Jeng MJ   Liu Rai-Shung RS  

Chemical science 20190522 26


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 indolizin  ...[more]

Similar Datasets

| S-EPMC3090038 | biostudies-literature
| S-EPMC5542682 | biostudies-literature
| S-EPMC3107521 | biostudies-literature
| S-EPMC2774260 | biostudies-literature
| S-EPMC6548424 | biostudies-literature
| S-EPMC5822218 | biostudies-literature
| S-EPMC7997634 | biostudies-literature
| S-EPMC3163120 | biostudies-literature
| S-EPMC8152626 | biostudies-literature
| S-EPMC5915799 | biostudies-literature