1226985-26-7Relevant academic research and scientific papers
Regio- And Enantioselective Iridium-Catalyzed Amination of Alkyl-Substituted Allylic Acetates with Secondary Amines
Jung, Woo-Ok,Yoo, Minjin,Migliozzi, Madyson M.,Zbieg, Jason R.,Stivala, Craig E.,Krische, Michael J.
supporting information, p. 441 - 445 (2021/12/27)
Robust air-stable cyclometalated π-allyliridium C,O-benzoates modified by (S)-tol-BINAP catalyze the reaction of secondary aliphatic amines with racemic alkyl-substituted allylic acetates to furnish products of allylic amination with high levels of enantioselectivity. Complete branched regioselectivities were observed despite the formation of more highly substituted C-N bonds.
Hydroxymethylation beyond Carbonylation: Enantioselective Iridium-Catalyzed Reductive Coupling of Formaldehyde with Allylic Acetates via Enantiotopic π-Facial Discrimination
Garza, Victoria J.,Krische, Michael J.
supporting information, p. 3655 - 3658 (2016/04/09)
Chiral iridium complexes modified by SEGPHOS catalyze the 2-propanol-mediated reductive coupling of branched allylic acetates 1a-1o with formaldehyde to form primary homoallylic alcohols 2a-2o with excellent control of regio- and enantioselectivity. These
Stereoselective total synthesis of seimatopolide a
Bhunia, Nisith,Das, Biswanath
, p. 1633 - 1642 (2014/01/17)
Stereoselective total synthesis of the naturally occurring bioactive macrolide, seimatopolide A has been achieved starting from commercially available (+)-diethyl tartrate. Chelation-controlled Grignard reaction, Yamaguchi esterification, ring closing cross metathesis and CBS reduction reactions are involved as key steps.
Towards the synthesis of the 4,19-diol derivative of (-)-mycothiazole: Synthesis of a potential key intermediate
Batt, Frederic,Fache, Fabienne
, p. 6039 - 6055 (2011/12/15)
The synthesis of a potential key intermediate for the synthesis of the 4,19-diol derivative of (-)-mycothiazole using convergent strategies is described in this paper. Several approaches have been tested, including cross metathesis and a Julia-Kocienski olefination. Finally, the formation of the 1,1-dialkyl-1,2-ethanediol motif through C4-C5 bond construction was realized by nucleophilic addition of a vinyl iodide derivative to a keto ester after halogen/lithium exchange followed by reduction of the resulting hydroxy ester. The synthesis of the allylic 1,1-dialkyl-1,2-ethanediol group, achieved by halogen/metal exchange followed by addition to aα-keto ester, is the key step of this convergent strategy towards a potential intermediate of mycothiazole-4,19-diol.
Nickel-catalyzed allylic substitution of simple alkenes
Matsubara, Ryosuke,Jamison, Timothy F.
supporting information; experimental part, p. 1860 - 1875 (2012/02/02)
This report describes a nickel-catalyzed allylic substitution process of simple alkenes whereby an important structural motif, a 1,4-diene, was prepared. The key to success is the use of an appropriate nickel-phosphine complex and a stoichiometric amount of silyl triflate. Reactions of 1-alkyl-substituted alkenes consistently provided 1,1-disubstituted alkenes with high selectivity. Insight into the reaction mechanism as well as miscellaneous application of the developed catalytic process is also documented.
Nickel-catalyzed allylic substitution of simple alkenes
Matsubara, Ryosuke,Jamison, Timothy F.
supporting information; experimental part, p. 6880 - 6881 (2010/07/05)
Nickel-catalyzed intermolecular allylic substitution of simple alkenes (ethylene and alpha olefins) is described. This method is the first catalytic intermolecular process for direct allylation of nonconjugated, nonstrained simple alkenes. Catalyst loadings as low as 2.5 mol % Ni afford the desired product in high yield in both gram-scale and smaller scale coupling reactions.
First asymmetric synthesis of achaetolide
Das, Tapas,Bhuniya, Rajib,Nanda, Samik
experimental part, p. 2206 - 2211 (2010/11/04)
The first asymmetric synthesis of the 10-membered macrolide achaetolide is reported in this article. The main highlight of the synthetic strategy is the ring-closing metathesis (RCM) of intermediate 19, which in turn can be accessed from coupling between alcohol 11 and acid 18. The synthesis of 11 involves enzymatic kinetic resolution (EKR) coupled with a Mitsunobu inversion strategy, while 18 can be prepared by adopting a metal-enzyme combined dynamic kinetic resolution (DKR) reaction followed by functional group manipulation.
Antiviral activity enhancement through the SATE prodrug of a 2′-modified 5′-norcarbocyclic adenine analogue
Li, Hua,Kim, Si Wouk,Hong, Joon Hee
experimental part, p. 2180 - 2184 (2010/11/18)
We synthesized and tested the anti-HIV activity of the SATE prodrug of a 2′-methyl 5′-norcarbocyclic adenine analogue. The introduction of a methyl group in the 2′-position was performed by the addition of a carbonyl using isopropenyl magnesium bromide. T
