137333-75-6Relevant academic research and scientific papers
Chemo- and stereoselective six-membered oxonium ylide formation–[2,3]-sigmatropic rearrangement of 2-diazo-3-ketoesters with dirhodium(II) catalyst and its application to the synthesis of (+)-tanikolide
Jinnouchi, Hikari,Nambu, Hisanori,Takahashi, Kanae,Fujiwara, Tomoya,Yakura, Takayuki
, p. 2436 - 2445 (2019)
Dirhodium(II)-catalyzed oxonium ylide formation–[2,3]-sigmatropic rearrangement of 6-allyloxy-2-diazo-3-ketoesters possessing a C-6 substituent is described. The reaction of 6-alkyl- or 6-aryl-substituted 6-allyloxy-2-diazo-3-ketoesters with a catalytic amount of Rh2(S-PTTL)4 proceeded in a chemoselective and stereoselective manner to provide 6-substituted 2-allyl-3-oxotetrahydropyran-2-carboxylates in good yields and with high diastereoselectivities. To demonstrate the utility of this sequential reaction, we conducted the total synthesis of (+)-tanikolide, in which the construction of the δ-lactone skeleton was achieved by employing a 2-iodobenzamide-catalyzed oxidative cleavage of tetrahydropyran-2-methanol.
Chemoselective Deoxygenation of 2° Benzylic Alcohols through a Sequence of Formylation and B(C6F5)3-Catalyzed Reduction
Oestreich, Martin,Richter, Sven C.
supporting information, p. 2103 - 2106 (2021/07/22)
A sequence of formylation and B(C6F5)3-catalyzed reduction of the resulting formate with Et3SiH enables the chemoselective deoxygenation of secondary benzylic alcohols. Primary benzylic and tertiary non-benzylic alcohols are not reduced by this protocol. The formyl group fulfills a double role as activator and self-sacrificing protecting group. The deoxygenation of these formates is fast and can be carried out in the presence of other potentially reducible groups. Neighboring-group participation was found in the deoxygenation of certain diol motifs.
Stereoselective construction of 2,6- cis -disubstituted tetrahydropyrans via intramolecular amide enolate alkylation: Total synthesis of (-)-centrolobine
Latif, Muhammad,Yun, Jeong In,Seshadri, Kalapati,Kim, Hyoung Rae,Park, Chi Hoon,Park, Haeil,Kim, Hyoungsu,Lee, Jongkook
, p. 3315 - 3320 (2015/03/30)
A highly stereoselective construction of 2,6-cis-disubstituted tetrahydropyrans was achieved by using an intramolecular amide enolate alkylation with KHMDS. The efficiency and practicality of this methodology was successfully demonstrated in the total syn
Nickel-catalyzed reductive cyclization of organohalides
Kim, Hyejin,Lee, Chulbom
supporting information; experimental part, p. 2050 - 2053 (2011/06/25)
A mild and convenient nickel-catalyzed method for free-radical cyclization of organohalides is described. The use of a NiCl2DME/Pybox complex as the catalyst and zinc powder in methanol efficiently promotes the reductive cyclization of various
Bistriphenylsilanol-assisted oxidation catalyzed by chromium(VI) oxide of activated trimethyl ethers with tert-butyl hydroperoxide
Muzart,N'Ait Ajjou
, p. 1993 - 1996 (2007/10/02)
Secondary benzylic or allylic trimetylsilyl ethers are oxidized at room temperature to the corresponding ketones in good yields using aqueous 70% t-BuOOH and catalytic amounts of a mixture of Ph3SiOH and CrO3.
