70451-01-3Relevant academic research and scientific papers
Nucleophilic Substitutions of Alcohols in High Levels of Catalytic Efficiency
Stach, Tanja,Dr?ger, Julia,Huy, Peter H.
supporting information, p. 2980 - 2983 (2018/05/28)
A practical method for the nucleophilic substitution (SN) of alcohols furnishing alkyl chlorides, bromides, and iodides under stereochemical inversion in high catalytic efficacy is introduced. The fusion of diethylcyclopropenone as a simple Lewis base organocatalyst and benzoyl chloride as a reagent allows notable turnover numbers up to 100. Moreover, the use of plain acetyl chloride as a stoichiometric promotor in an invertive SN-type transformation is demonstrated for the first time. The operationally straightforward protocol exhibits high levels of stereoselectivity and scalability and tolerates a variety of functional groups.
Ester Formation via Nickel-Catalyzed Reductive Coupling of Alkyl Halides with Chloroformates
Zheng, Min,Xue, Weichao,Xue, Teng,Gong, Hegui
supporting information, p. 6152 - 6155 (2016/12/09)
The synthesis of alkyl esters from readily available alkyl halides and chloroformates was achieved for the first time using a mild Ni-catalyzed reductive coupling protocol. Unactivated primary and secondary alkyl iodides as well as glycosyl, benzyl, and aminomethyl halides were successfully employed to yield products in moderate to excellent yields with high functional group tolerance.
Total synthesis of tubulysins U and V
Sani, Monica,Fossati, Giacomo,Huguenot, Florent,Zanda, Matteo
, p. 3526 - 3529 (2008/03/11)
Meeting the challenge: A reliable and modular reaction sequence has been developed for the synthesis of the challenging tubulysin framework. This route allows preparation of hundreds of milligrams of the stereochemically pure tetrapeptides (see picture), which are produced in small amounts by two different species of myxobacteria. Thus, full biological evaluation of the tubulysins and their analogues is now a real possibility. (Chemical Equation Presented).
A versatile annulation protocol toward novel constrained phosphinic peptidomimetics
Nasopoulou, Magdalini,Georgiadis, Dimitris,Matziari, Magdalini,Dive, Vincent,Yiotakis, Athanasios
, p. 7222 - 7228 (2008/02/12)
(Chemical Equation Presented) The development of a novel 3-center 2-component annulation reaction between α,ω-carbamoylaldehydes and suitably monoalkylated phosphinic acids is reported. Depending on the starting α,ω-carbamoylaldehyde, diverse phosphinic scaffolds varying in the size of their rigidity element, the nature and stereochemistry of substituents, and the participation of heteroatoms in the azacyclic ring system can be obtained in one synthetic step and in high yield. In addition, this methodology allows the synthesis of Fmoc-protected constrained aminophosphinic acids that can be easily converted to suitable pseudodipeptide building blocks compatible with the requirements of peptide synthesis on the solid phase. Finally, the careful choice of both substituents and protecting groups can provide functionally diverse, orthogonally protected constrained scaffolds for extended derivatization of the target phosphinic peptidomimetic structrures.
Thiazole compounds and methods of use
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Page/Page column 30-31; 31, (2008/06/13)
The invention relates to thiazole compounds of Formula I and Formula II and compositions thereof useful for treating diseases mediated by protein kinase B (PKB) where the variables have the definitions provided herein. The invention also relates to the therapeutic use of such thiazole compounds and compositions thereof in treating disease states associated with abnormal cell growth, cancer, inflammation, and metabolic disorders.
Methyl 2-((succinimidooxy)carbonyl)benzoate (MSB): a new, efficient reagent for N-phthaloylation of amino acid and peptide derivatives.
Casimir, J Richard,Guichard, Gilles,Briand, Jean-Paul
, p. 3764 - 3768 (2007/10/03)
A new, efficient, and readily available reagent, methyl 2-((succinimidooxy)carbonyl)benzoate (MSB), for N-phthaloylation of amino acids and amino acid derivatives is described. The phthaloylation procedure is simple and racemization-free and gives excellent results with alpha-amino acids, alpha-amino alcohols, dipeptides, alpha-amino carboxamides, and alpha-amino esters.
Diastereoselective access to chiral non-racemic [1,3]oxazolo-[2,3-a] isoindol-5-one ring systems via o-cationic cyclization
Sikoraiova, Jana,Chihab-Eddine, Abderrahim,Marchalin, Stefan,Daich, Adam
, p. 383 - 390 (2007/10/03)
The title compounds 4 have been prepared from suitable β-amino-alcohol 2 and phthalic anhydride (5) in a three-step sequence in moderate to good yields (58-94%). The key step of this methodology is based on an intramolecular O-cationic cyclization involving N-acyliminium species. The high levels of the observed chemoselectivity during the intermolecular or intramolecular cyclization were also discussed.
Rapid procedure for N-phthaloylation of α-amino carboxamides, α-amino alcohols, α-amino esters and dipeptide derivatives
Casimir,Guichard,Tourwe,Briand
, p. 1985 - 1988 (2007/10/03)
A rapid, one-pot synthesis and mild procedure for the N-phthaloylation of α-amino carboxamides is described. In acetonitrile, these derivatives react with mono-methylphthalate in the presence of BOP and i-Pr2NEt to afford the intermediate Nα-[(o-methoxycarbonyl)benzoyl]amino carboxamides, which undergo rapid cyclization in the presence of aqueous sodium carbonate to afford the corresponding Nα-phthaloylamino carboxamides in excellent yields. The reaction also works efficiently with α-amino esters, α-amino alcohols and dipeptide esters or amides.
Stereospecific synthesis of mexiletine and related compounds: Mitsunobu versus Williamson reaction
Carocci, Alessia,Catalano, Alessia,Corbo, Filomena,Duranti, Andrea,Amoroso, Rosa,Franchini, Carlo,Lentini, Giovanni,Tortorella, Vincenzo
, p. 3619 - 3634 (2007/10/03)
Mexiletine [1-(2,6-dimethylphenoxy)-2-propanamine], a chiral, orally effective antiarrhythmic agent, and several analogues substituted on either the stereogenic centre or the xylyloxy moiety, were prepared in both, highly enriched, optically active forms. According to the 'chiral pool' approach, the appropriate amino alcohols, protected as the corresponding phthalimide derivatives, were condensed with the desired phenols under either Mitsunobu (method A) or Williamson (method B) conditions. Generally, method A provided the most efficient route, both in terms of yields and number of steps necessary. Only when an isopropyl group was present on the stereogenic centre, i.e. when 2-amino-3-methylbutanol was used as the starting alcohol, method B proved to be the only available route, method A giving no product other than the starting phthalimide derivative. Regardless of the method used, enantiomeric excesses ranged from 91 to 99%. Given the availability of both variously substituted phenols and optically active amino alcohols, the two methods described herein, taken together, may serve as a versatile approach, useful to meet the needs of new chiral, optically active mexiletine analogues, possibly endowed with higher potency in exerting a use-dependent block on sodium channels and/or more resistant to biotransformations. Copyright (C) 2000 Elsevier Science Ltd.
An Unusual Acyliminium Cyclization and Other Drawbacks during an Attempted Synthesis of a Chiral Primary α-Phosphinoalkanamine
Christoffers, Jens
, p. 845 - 852 (2007/10/03)
Studies towards the synthesis of a chiral primary α-phosphinoalkanamine 1a are reported. O-Activated, N-carbamate-protected phenylalaninol 3a did not undergo 5N reaction with KPPh2: instead, after TV-deprotonalion, intramolecular substitution led to formation of the aziridine derivative 5a (Scheme 2). N-Phthalimido-protected. O-activated phenylalaninol 3b also underwent an intramolecular process on treatment with KPPh2, i.e., an unusual aryl-acyliminium cyclization furnishing the (epoxymethano)isoindolo[1,2-a]isoquinolinone 7 (Scheme 3). In a reaction with KPPh2, the N,N-dibenzyl-protected and activated phenylalaninol 3d finally yielded the intermolecular SN reaction product 2a (Scheme 4). However, debenzylation by catalytic hydrogenation turned out to be impossible.
