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Cyclization Reaction for the Synthesis of Polysubstituted Naphthalenes in the Presence of Au(I) Precatalysts

Title
Cyclization Reaction for the Synthesis of Polysubstituted Naphthalenes in the Presence of Au(I) Precatalysts
Author
윤소원
Keywords
ACTIVATED METHYLENE-COMPOUNDS; NAPHTHYL KETONE DERIVATIVES; LEWIS-ACID; SUBSTITUTED NAPHTHALENES; REGIOSELECTIVE SYNTHESIS; ORGANIC TRANSFORMATIONS; INTRAMOLECULAR ADDITION; CLAISEN REARRANGEMENT; MEDIATED CYCLIZATION; UNACTIVATED OLEFINS
Issue Date
2011-09
Publisher
AMER CHEMICAL SOC, 1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Citation
Journal of Organic Chemistry, Vol.76, No.17 [2011], p7204-7215
Abstract
Au(I)-catalyzed cyclization of alkenyl carbonyl compounds leading to a variety of substituted naphthalenes has been developed. This process exploits a dual function of the Au(I) catalyst: (1) the oxophilic nature of the Au(I) catalyst, counterintuitive to the pi-acidic reactivities generally associated with Au catalysts, and (2) olefin isomerization supported by the outcome of isotope scrambling experiments. It cannot be completely excluded that TfOH is a true operative catalyst in this protocol. In view of the practicality, the unnecessity of isomerically pure starting material in this reaction is particularly attractive and valuable.
URI
https://pubs.acs.org/doi/abs/10.1021/jo201339zhttp://hdl.handle.net/20.500.11754/37426
ISSN
0022-3263
DOI
10.1021/jo201339z
Appears in Collections:
COLLEGE OF NATURAL SCIENCES[S](자연과학대학) > CHEMISTRY(화학과) > Articles
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