838906-52-8Relevant academic research and scientific papers
Oxonium ylide rearrangement of enzymatically desymmetrized glutarates
Skrobo, Benedikt,Deska, Jan
, p. 5998 - 6001 (2013)
The combination of an enzyme-mediated enantioselective desymmetrization of readily available 3-benzyloxyglutarates and subsequent rhodium-catalyzed oxonium ylide rearrangement of their corresponding in situ derived diazo ketones offers a very concise and highly stereoselective access to functionalized tetrahydrofuranone building blocks.
Stereoselective synthesis of alicyclic ketones: A hydrogen borrowing approach
Armstrong, Roly J.,Akhtar, Wasim M.,Frost, James R.,Christensen, Kirsten E.,Stevenson, Neil G.,Donohoe, Timothy J.
supporting information, (2019/11/13)
A highly diastereoselective annulation strategy for the synthesis of alicyclic ketones from diols and pentamethylacetophenone is described. This process is mediated by a commercially available iridium(III) catalyst, and provides efficient access to a wide range of cyclopentane and cyclohexane products with high levels of stereoselectivity. The origins of diastereoselectivity in the annulation reaction have been explored by a series of control experiments, which provides an explanation for how each stereocentre around the newly forged ring is controlled.
Kirmse–Doyle- and Stevens-Type Rearrangements of Glutarate-Derived Oxonium Ylides
Skrobo, Benedikt,Schl?rer, Nils E.,Neud?rfl, J?rg -M.,Deska, Jan
supporting information, p. 3209 - 3217 (2018/02/09)
A novel chemoenzymatic synthetic cascade enables the preparation of densely decorated tetrahydrofuran building blocks. Here, the lipase-catalyzed desymmetrization of 3-alkoxyglutarates renders highly enantioenriched carboxylic acid intermediates, whose subsequent activation and oxonium ylide rearrangement by means of rhodium or copper complexes furnishes functionalized O-heterocycles with excellent diastereoselectivity. The two-step protocol offers a streamlined and flexible synthesis of tetrahydrofuranones bearing different benzylic, allylic or allenylic side chains with full control over multiple stereogenic centers.
Synthesis of GABOB and GABOB-Based Chiral Units Possessing Distinct Protecting Groups
Ivic, Trpimir,Dokli, Irena,Rimac, Ana,Hamerak, Zdenko
, p. 631 - 638 (2015/10/05)
In addition to the varied biological activity of GABOB (4-amino-3-hydroxybutanoic acid), the structure of its protected derivatives makes them interesting chiral intermediates for the synthesis of more complex compounds. A stereoselective route to GABOB derivatives with three different protecting groups is presented, using anhydride desymmetrization as a chirality-inducing step. Selective removal of the protecting groups gave compounds with a free carboxylic acid or hydroxy group. Removal of all of the protecting groups allowed GABOB to be isolated in good yield and with excellent ee.
Synthesis of GABOB and GABOB-based chiral units possessing distinct protecting groups
Ivsic, Trpimir,Dokli, Irena,Rimac, Ana,Hamersak, Zdenko
, p. 631 - 638 (2014/02/14)
In addition to the varied biological activity of GABOB (4-amino-3- hydroxybutanoic acid), the structure of its protected derivatives makes them interesting chiral intermediates for the synthesis of more complex compounds. A stereoselective route to GABOB derivatives with three different protecting groups is presented, using anhydride desymmetrization as a chirality-inducing step. Selective removal of the protecting groups gave compounds with a free carboxylic acid or hydroxy group. Removal of all of the protecting groups allowed GABOB to be isolated in good yield and with excellent ee. A stereoselective route to GABOB (4-amino-3-hydroxybutanoic acid) derivatives with three different protecting groups is presented. Selective deprotection produced diprotected chiral building blocks with a free carboxylic acid or hydroxy group. Removal of all the protecting groups allowed GABOB to be isolated. Copyright
Asymmetric synthesis of the HMG-CoA reductase inhibitor atorvastatin calcium: An organocatalytic anhydride desymmetrization and cyanide-free side chain elongation approach
Chen, Xiaofei,Xiong, Fangjun,Chen, Wenxue,He, Qiuqin,Chen, Fener
, p. 2723 - 2728 (2014/04/17)
An efficient asymmetric synthesis of atorvastatin calcium has been achieved from commercially available diethyl 3-hydroxyglutarate through a novel approach that involves an organocatalytic enantioselective cyclic anhydride desymmetrization to establish C(
Synthesis of 3-substituted tetrahydrofuran and 4-substituted tetrahydropyran derivatives by cyclization of dicarboxylic acids with InBr 3/TMDS
Pehlivan, Leyla,Metay, Estelle,Delbrayelle, Dominique,Mignani, Gerard,Lemaire, Marc
supporting information; experimental part, p. 4689 - 4693 (2012/09/22)
An efficient reduction followed by cyclization of diacid compounds with the InBr3/TMDS system is reported. This system allows the formation of five- and six-membered ring ethers substituted in the 3- or 4-position. Copyright
Highly efficient nickel-catalyzed cross-coupling of succinic and glutaric anhydrides with organozinc reagents
Bercot, Eric A.,Rovis, Tomislav
, p. 247 - 254 (2007/10/03)
A nickel-catalyzed alkylation of succinic and glutaric anhydrides with alkyl- and arylzinc reagents has been developed. A dramatic olefin effect has been investigated resulting in the identification of several styrene-based promoters which show pronounced enhancements in reaction rate. The substrate scope with respect to electrophilic and nucleophilic coupling partners has been examined and found to be remarkably broad, allowing for rapid introduction of molecular complexity through the use of functionalized coupling partners. Regioselective alkylation of an unsymmetrical succinic anhydride and a profound effect of pendent coordinating olefins on reaction rate suggest a mechanism involving discrete oxidative addition of the nickel complex into the cyclic anhydride followed by a transmetalation event.
