5272-36-6Relevant articles and documents
Synthesis of cyclic polyelectrolyte via direct copper(I)-catalyzed click cyclization
Chen, Fenggui,Liu, Guangming,Zhang, Guangzhao
, p. 831 - 835 (2012)
Well-defined cyclic poly(acrylic acid) (PAA) has been successfully prepared based on the direct click cyclization. The linear poly(tert-butyl acrylate) (PtBA) with azide and TMS-protected alkyne group forms cyclic chain directly by the copper(I)-catalyzed click cyclization without any deprotection steps. Cyclic PAA is synthesized by the hydrolysis of cyclic PtBA. The present synthetic strategy provides a simple and efficient method to synthesize cyclic polyelectrolyte and can be applied to other polymer systems. Copyright
Silver-catalyzed heterocyclization: First total synthesis of the naturally occurring cis 2-hexadecyl-3-hydroxy-4-methylene butyrolactone
Dalla,Pale
, p. 3525 - 3528 (1994)
The title compound was obtained in 4 steps with an overall yield of 64% with the silver-catalyzed cyclization of the corresponding substituted β-hydroxy-γ-acetylenic acid as the key step.
Silicon-directed decarbonylation of trimethylsilyl β,γ-enals by photolysis
Hwu,Furth
, p. 8834 - 8841 (1989)
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Ni-catalyzed direct carboxylation of propargylic alcohols with carbon dioxide
Yamahira, Tatsuya,Onodera, Gen,Fukuda, Tsutomu,Kimura, Masanari
supporting information, p. 853 - 855 (2021/05/19)
The carboxylation of propargylic alcohols containing a silyl group at the terminal position was conducted in a CO2 atmosphere at atmospheric pressure in the presence of a nickel catalyst and diethylzinc. Here, CO2 was used as not only the C1 source but also the promoter of the COH cleavage processes for the oxidative addition of propargylic alcohols.
Development of a Radical Silylzincation of (Het)Aryl-Substituted Alkynes and Computational Insights into the Origin of the trans-Stereoselectivity
Romain, Elise,de la Vega-Hernández, Karen,Guégan, Frédéric,Sanz García, Juan,Fopp, Carolin,Chemla, Fabrice,Ferreira, Franck,Gerard, Hélène,Jackowski, Olivier,Halbert, Stéphanie,Oestreich, Martin,Perez-Luna, Alejandro
supporting information, p. 2634 - 2647 (2021/03/30)
Aryl- and hetaryl-substituted acetylenes undergo regio- and stereoselective silylzincation by reaction with [(Me3Si)3Si]2Zn in the presence of Et2Zn (10–110 mol%) as additive. The distinctive feature of this addition across the C?C triple bond is its trans stereoselectivity. The radical nature of the silylzincation process is supported by diagnostic experiments and DFT calculations, which also corroborate the role played by steric effects to obtain that stereoselectivity. The procedure can be combined in one-pot with the copper(I)-mediated electrophilic substitution of the C(sp2)?Zn bond, with retention of the double bond geometry. This makes it valuable for the synthesis of stereodefined di- and trisubstituted vinylsilanes. (Figure presented.).
Catalytic Asymmetric Total Synthesis of Exiguolide
Oka, Kengo,Fuchi, Shunsuke,Komine, Keita,Fukuda, Hayato,Hatakeyama, Susumi,Ishihara, Jun
supporting information, p. 12862 - 12867 (2020/09/16)
The catalytic asymmetric total synthesis of (?)-exiguolide, a complex 20-membered macrolide embedded with a bis(tetrahydropyran) motif, is reported. The convergent synthesis involves the construction of the C1–C11 tetrahydropyran segment via catalytic asymmetric allylation and Prins cyclization, and the formation of the C12–C21 phosphonate segment via catalytic asymmetric cyclocondensation reaction and Johnson–Claisen rearrangement. The synthesis of 15-epi-exiguolide is also described.
