propargylic alcohol
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Synlett ◽  
2021 ◽  
Author(s):  
Narihito Ogawa ◽  
Kohei Arai ◽  
Yuichi Kobayashi

AbstractA total synthesis of resolvin T4 was achieved by connecting three intermediates by Wittig reactions. The enal in the C1–C10 part was constructed through reduction of a propargylic alcohol with Red-Al followed by oxidation. The enal moiety in the C11–C16 part was synthesized by a ring-opening reaction of a silyl epoxide followed by a Peterson elimination. The chiral centers at C7 and C13 were constructed by ruthenium-catalyzed asymmetric transfer hydrogenation.


2021 ◽  
Vol 99 (2) ◽  
pp. 268-276
Author(s):  
Sunny Kai San Tse ◽  
Herman Ho-Yung Sung ◽  
Ian Duncan Williams ◽  
Guochen Jia

Reactions of Cp*OsCl(PPh3)2 (Cp* = pentamethylcyclopentadienyl) with alkynes and alkynols are described. Treatment of Cp*OsCl(PPh3)2 with phenylacetylene and trimethylsilylacetylene gave the vinylidene complexes Cp*OsCl(=C=CHPh)(PPh3) and Cp*OsCl(=C=CH2)(PPh3), respectively. Treatment of Cp*OsCl(PPh3)2 with the internal alkyne dimethyl acetylenedicarboxylate produced the η2-alkyne complex Cp*OsCl(η2-MeO2C≡CCO2Me)(PPh3). Treatment of Cp*OsCl(PPh3)2 with the propargylic alcohol HC≡CC(OH)Ph2 gave the osmium allenylidene complex Cp*OsCl(=C = C=CPh2)(PPh3). The outcomes of the reactions of Cp*OsCl(PPh3)2 with ω-alkynols HC≡C(CH2)nOH are dependent on the length of the -(CH2)n- linker. The reaction with 3-butyn-1-ol produced the cyclic oxycarbene complex Cp*OsCl{=C(CH2)3O}(PPh3) exclusively. The reactions with 4-pentyn-1-ol produced a mixture of the hydroxyalkyl vinylidene complex Cp*OsCl{=C=CH(CH2)3OH}(PPh3) and the cyclic oxycarbene complex Cp*OsCl{=C(CH2)4O}(PPh3) in about 10:1 molar ratio. The reaction with 5-hexyn-1-ol gave exclusively the hydroxyalkyl vinylidene complex Cp*OsCl{=C=CH(CH2)4OH}(PPh3).


2021 ◽  
Author(s):  
Yi-Feng Zhang ◽  
Wei-Ming Lai ◽  
Sheng Xie ◽  
Hui Zhou ◽  
Xiaobing Lu

Herein, we present a facile and effective method for the synthesis of CO2-sourced sequence-controlled poly(thioether-co-carbonate)s via consecutive organocatalyzed carboxylative cyclization of vinyl-functionalized propargylic alcohol with CO2, ring-opening transesterification of the...


Author(s):  
Ziyang Wang ◽  
Xiao Lin ◽  
Xuling Chen ◽  
Pengfei Li ◽  
Wenjun Li

A chiral phosphoric acid catalyzed enantioselective 1,6-conjugate addition of thiolacetic acid to propargylic indole imine methide in situ formed from α-(3-indolyl) propargylic alcohol has been established, which enables the formation...


Author(s):  
Asaki Miyairi ◽  
Yoshihiro Oonishi ◽  
Yoshihiro Sato

One-pot synthesis of fully substituted 2-aminofurans via a Au(I)-catalyzed cascade reaction of ynamides and propargylic alcohol was realized. Hydroalkoxylation of ynamide with propargylic alcohol, Saucy-Marbet rearrangement, and cyclization of the...


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