Synthesis of γ-substituted carbonyl compounds from DMSO-mediated oxidation of enynamides: Mechanistic insights and carbon- and hetero-functionalizationsopen access
- Authors
- Nguyen, Quynh H.; Nguyen, Nguyen H.; Kim, Hanbyul; Shin, Seunghoon
- Issue Date
- Oct-2019
- Publisher
- ROYAL SOC CHEMISTRY
- Citation
- CHEMICAL SCIENCE, v.10, no.38, pp.8799 - 8805
- Indexed
- SCIE
SCOPUS
- Journal Title
- CHEMICAL SCIENCE
- Volume
- 10
- Number
- 38
- Start Page
- 8799
- End Page
- 8805
- URI
- https://scholarworks.bwise.kr/hanyang/handle/2021.sw.hanyang/147069
- DOI
- 10.1039/c9sc03663f
- ISSN
- 2041-6520
- Abstract
- Oxidative coupling of 1,3-enynamides using DMSO as a terminal oxidant has been developed. Carbon as well as unmodified heteroatom nucleophiles, including aliphatic alcohols, thiols, and hydrazides, could be efficiently alkylated at the gamma-position in a highly regioselective fashion. The kinetic analysis suggested a nucleophile-dependent mechanism ranging from a concerted S(N)2 '' to a carbocationic mechanism. Thus, the remote site-selectivity was ascribed to the partial positive charge developing at the terminal carbocationic center.
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