93780-03-1Relevant articles and documents
Dual Activation of Unsaturated Amides with Schwartz's Reagent: A Diastereoselective Access to Cyclopentanols and N,O-Dimethylcyclopentylhydroxylamines.
Coelho, Aurélien,Souvenir Zafindrajaona, Mahasoa-Salina,Vallée, Alexis,Behr, Jean-Bernard,Vasse, Jean-Luc
supporting information, (2021/12/06)
The diastereoselective access to cyclopentanols and N,O-dimethylcyclopentylhydroxylamines from 4-pentenoic acid-derived Weinreb amides is described. Based on the concomitant generation of both the nucleophilic and the electrophilic poles by hydrozirconati
Convergent Evolution of Diastereomeric Mixtures of 5-Methoxy-pentylzirconocenes toward Trans-1,2-substituted Cyclopentanes
Coelho, Aurélien,Machado-Rodrigues, Carine,Behr, Jean-Bernard,Vasse, Jean-Luc
supporting information, p. 772 - 776 (2021/02/01)
The access to 1,2- and 1,1,2-substituted trans cyclopentanes via a sequential hydrozirconation/TMSOTf-mediated cyclization applied to 5-methoxypent-1-enes is presented. Involving a transient carbocation, the reaction was shown to be diastereo-convergent. Possibly performed in a nonracemic version, the reaction proved compatible with a range of functional groups affording a large panel of cyclopentanes.
Soluble polymer supported 2-imidazolidinone chiral auxiliary and method for manufacturing the same
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Paragraph 0092; 0097-0101, (2017/01/02)
The present invention relates to a chiral auxiliary agent and a manufacturing method thereof and, more specifically, to a 2-imidazolidinone chiral auxiliary agent supported onto a polymer soluble in an organic solvent and a manufacturing method thereof. The chiral auxiliary agent in the present invention shows effects of being easy to separate reaction products and the chiral auxiliary agent after a termination of a reaction while fulfilling an economic efficacy of chiral auxiliary molecules by being supported onto the polymer soluble in the organic solvent.COPYRIGHT KIPO 2015
Solid phase asymmetric alkylation reactions using 2-imidazolidinone chiral auxiliary
Nguyen, Quynh Pham Bao,Kim, Jae Nyoung,Kim, Taek Hyeon
scheme or table, p. 4015 - 4018 (2009/11/30)
A novel solid supported 2-imidazolidinone chiral auxiliary was prepared from O-benzyl-l-tyrosine and Wang resin. Asymmetric alkylation reactions in the solid phase proceeded with excellent stereoselectivities, which were even higher than those observed in the conventional solution phase method.
Fluorine-directed diastereoselective iodocyclizations
Tredwell, Matthew,Luft, Jennifer A. R.,Schuler, Marie,Tenza, Kenny,Houk, Kendall N.,Gouverneur, Veronique
, p. 357 - 360 (2008/09/19)
(Chemical Equation Presented) An inside job: β-Fluorinated lactones and tetrahydrofurans are synthesized by iodocyclization of various allylic fluorides. The fluorine substituent acts as a highly efficient syn-stereodirecting group for the ring closure. T
Remarkable electronic and steric effects in the nitrile biotransformations for the preparation of enantiopure functionalized carboxylic acids and amides: Implication for an unsaturated carbon-carbon bond binding domain of the amidase
Gao, Ming,Wang, De-Xian,Zheng, Qi-Yu,Huang, Zhi-Tang,Wang, Mei-Xiang
, p. 6060 - 6066 (2008/02/10)
(Chemical Equation Presented) Biotransformations of various functionalized racemic nitriles catalyzed by Rhodococcus erythropolis AJ270, a nitrile hydratase/amidase-containing microbial whole-cell catalyst, were studied. While the nitrile hydratase exhibi
Design and synthesis of a new polymer-supported Evans-type oxazolidinone: An efficient chiral auxiliary in the solid-ph ase asymmetric alkylation reactions
Kotake, Tomoya,Hayashi, Yoshio,Rajesh,Mukai, Yoshie,Takiguchi, Yuka,Kimura, Tooru,Kiso, Yoshiaki
, p. 3819 - 3833 (2007/10/03)
Wang resin-supported Evans' chiral auxiliary (23) was designed based on a novel polymer-anchoring strategy, which utilizes the 5-position of the oxazolidinone ring, and its new synthetic route applicable to multi-gram preparation in just a day was developed. Solid-phase Evans' asymmetric alkylation on 23-derived N-acylimide resin and following lithium hydroperoxide-mediated chemoselective hydrolysis afforded the corresponding α-branched carboxylic acids in desired high stereoselectivities (up to 97% ee) and moderate to good overall yield (up to 70%, for 3 steps), which were comparable to those of the conventional solution-phase methods. Furthermore, recovery and recycling of the polymer-supported chiral auxiliary were successfully achieved without decreasing the stereoselectivity of the product. Therefore, this is the first successful example that the solid-phase Evans' asymmetric enolate-alkylation was efficiently performed on the solid-support, and it is concluded that the connection to the solid-support via the 5-position of the oxazolidinone ring is an ideal strategy in the solid-phase Evans' chiral auxiliary.
A new polymer-supported Evans-type chiral auxiliary derived from α-hydroxy-β-amino acid, phenylnorstatine: Synthesis and application in solid-phase asymmetric alkylation reactions
Kotake, Tomoya,Rajesh,Hayashi, Yoshio,Mukai, Yoshie,Ueda, Mitsuhiro,Kimura, Tooru,Kiso, Yoshiaki
, p. 3651 - 3654 (2007/10/03)
Based on a new anchoring strategy, a polymer-supported chiral oxazolidinone was prepared starting from (2R,3S)-3-amino-2-hydroxy-4-phenylbutanoic acid (phenylnorstatine, Pns) and Wang resin. Solid-phase asymmetric alkylation on this resin proceeded in high diastereoselectivity comparable to that of conventional solution-phase model experiments. This study suggests that anchoring through the 5-position of oxazolidinone is highly suited to achieving diastereoselective alkylation reactions on solid-support.
Relationship of stereochemical and skeletal diversity of small molecules to cellular measurement space
Kim, Young-Kwon,Arai, Midori A.,Arai, Takayoshi,Lamenzo, Julia O.,Dean III, Elton F.,Patterson, Nick,Clemons, Paul A.,Schreiber, Stuart L.
, p. 14740 - 14745 (2007/10/03)
Systematic and quantitative measurements of the roles of stereochemistry and skeleton-dependent conformational restriction were made using multidimensional screening. We first used diversity-oriented synthesis to synthesize the same number (122) of [10.4.
Asymmetric synthesis of intermediates for retroviral protease inhibitor compounds
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, (2008/06/13)
The disclosure describes an improved process for producing optically active compounds of Formula II or III, which compounds are useful as intermediates for preparing compounds active as inhibitors of retroviral protease enzymes: STR1 wherein R1