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Rh(III)-Catalyzed C8-Spiroannulation of 1-Aminonaphthalenes with Maleimides

Authors
Chung, EJ[Chung, Eunjae]Kim, S[Kim, Suho]Rakshit, A[Rakshit, Amitava]Singh, P[Singh, Pargat]Park, J[Park, Jaewook]Jeong, T[Jeong, Taejoo]Kim, IS[Kim, In Su]
Issue Date
18-Jul-2023
Publisher
AMER CHEMICAL SOC
Citation
JOURNAL OF ORGANIC CHEMISTRY, v.88, no.15, pp.11227 - 11239
Indexed
SCIE
SCOPUS
Journal Title
JOURNAL OF ORGANIC CHEMISTRY
Volume
88
Number
15
Start Page
11227
End Page
11239
URI
https://scholarworks.bwise.kr/skku/handle/2021.sw.skku/107292
DOI
10.1021/acs.joc.3c01258
ISSN
0022-3263
Abstract
The rhodium(III)-catalyzed C8-spiroannulation of 1-aminonaphthaleneswith maleimides is described herein. Initially formed C8-alkenylated1-aminonaphthalenes can intercept nucleophilic 1-amino groups throughthe intramolecular aza-Michael reaction, resulting in the formationof spirofused tetracyclic frameworks. This protocol displayed a widesubstrate scope and a broad functional group compatibility. The syntheticutility of this process is demonstrated by the gram-scale synthesis,late-stage modification, and synthetic transformations.
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