196407-30-4Relevant academic research and scientific papers
Gold-Catalyzed Oxidative Cyclizations of { o-(Alkynyl)phenyl propargyl} Silyl Ether Derivatives Involving 1,2-Enynyl Migration: Synthesis of Functionalized 1 H-Isochromenes and 2 H-Pyrans
Zhao, Jidong,Xu, Wei,Xie, Xin,Sun, Ning,Li, Xiangdong,Liu, Yuanhong
supporting information, p. 5461 - 5465 (2018/09/13)
A new and convenient strategy for the synthesis of functionalized 1H-isochromene and 2H-pyran derivatives based on gold-catalyzed oxidative cyclizations of o-(alkynyl)phenyl propargyl ether derivatives has been developed. The reaction proceeds via gold-catalyzed highly regioselective oxidation, followed by 1,2-migration of an enynyl group and nucleophlic addition. Isocoumarins were also constructed through oxidative cleavage of the exocyclic double bond of the obtained 1H-isochromenes.
Gold-catalyzed cascade friedel-crafts/furan-yne cyclization/heteroenyne metathesis for the highly efficient construction of phenanthrene derivatives
Chen, Yifeng,Li, Guijie,Liu, Yuanhong
supporting information; experimental part, p. 392 - 400 (2011/04/22)
A rapid access to highly substituted phenanthrenyl ketones through gold-catalyzed cyclization of 1,6-diyn-4-en-3-ols with furans has been developed. Gold catalysts are effective to catalyze three cascade processes involving Friedel-Crafts/furan-yne cyclization/heteroenyne metathesis through C-O bond and alkyne activation. This method offers several advantages such as high selectivities and easily accessible starting materials.
Ring size effects in the C2-C6 biradical cyclisation of enyne-allenes and the relevance for neocarzinostatin
Schmittel,Steffen,Maywald,Engels,Helten,Musch
, p. 1331 - 1339 (2007/10/03)
The regioselectivity of the thermal cyclisations of enyne-allenes 1 can be toggled as a function of the ring size of the cycloalkene. With a cyclopentene as the ene moiety the Myers-Saito (C2-C7) cycloaromatisation product is formed, whereas with six- and seven-membered cycloalkenes the novel C2-C6 cyclisation is observed. DFT calculations are used to rationalise these changes. The implications of these findings for alternative thermal biradical cyclisations of neocarzinostatin are discussed.
Ring strain effects in enyne-allene thermolysis: Switch from the Myers-Saito reaction to the C2-C6 biradical cyclization
Schmittel, Michael,Steffen, Jens-Peter,Auer, Dominik,Maywald, Michael
, p. 6177 - 6180 (2007/10/03)
The mode of the thermal cyclization of enyne-allenes 1 depends on ring strain effects: when the ene functionality is part of a benzene, cyclohexene or cycloheptene ring the novel C2-C6 biradical cyclization is observed, while when it is part of a cyclopentene ring the Myers-Saito cycloaromatization is registered.
