TY - JOUR
T1 - Late-Stage N-Alkenylative Modifications of Indolic Scaffolds with Propiolates
T2 - Toward Bisconjugation and Macrocyclization
AU - Chen, Xiaoye
AU - Au, Chi-Ming
AU - Fang, Pengyuan
AU - Xue, Yunsheng
AU - Leung, Ken Cham-Fai
AU - Chan, Wai-Lun
N1 - X.C., C.-M.A., P.F., and W.-L.C. appreciate Prof. Yixin Lu of the Department of Chemistry, National University Singapore, for academic and financial support. K.C.-F.L. is grateful to Hong Kong Baptist University (RMGS-2022-13-07) for financial support.
Publisher copyright:
© 2025 The Authors. Published by American Chemical Society.
PY - 2025/5/23
Y1 - 2025/5/23
N2 - A facile, mild, and scalable late-stage N-alkenylative modification strategy is introduced on 1H-indoles, 9H-carbazoles, and their structural derivatives and analogues, including alkaloids, bioactive agents, and tryptophan motifs, via chemo- and regioselective phosphine-mediated propiolate hydroamination. Saliently, through this protocol, bisconjugation and macrocyclization on (bis)indolic scaffolds can also be accomplished, with the installation of new α,β-unsaturated ester handles for potential further versatile synthetic manipulations.
AB - A facile, mild, and scalable late-stage N-alkenylative modification strategy is introduced on 1H-indoles, 9H-carbazoles, and their structural derivatives and analogues, including alkaloids, bioactive agents, and tryptophan motifs, via chemo- and regioselective phosphine-mediated propiolate hydroamination. Saliently, through this protocol, bisconjugation and macrocyclization on (bis)indolic scaffolds can also be accomplished, with the installation of new α,β-unsaturated ester handles for potential further versatile synthetic manipulations.
UR - http://www.scopus.com/inward/record.url?scp=105005439727&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.5c01162
DO - 10.1021/acs.orglett.5c01162
M3 - Journal article
C2 - 40368809
SN - 1523-7060
VL - 27
SP - 5081
EP - 5086
JO - Organic Letters
JF - Organic Letters
IS - 20
ER -
