52178-66-2Relevant academic research and scientific papers
Synthesis of highly-substituted enantiomerically pure allylboronic esters and investigation of their stereoselective addition to aldehydes
Vahabi, Roza,Frey, Wolfgang,Pietruszka, Joerg
, p. 11549 - 11559 (2013)
Diastereomerically pure allylboronates bearing the readily available tartrate derivative were obtained via sigmatropic rearrangement. Allyl additions were performed, and the influence of γ-disubstituted allylboronates was studied. Highly γ-substituted bor
3,3′-Bithiophene-Based Chiral Bisphosphine Oxides as Organocatalysts in Silicon-Derived Lewis Acid Mediated Reactions
Benaglia, Maurizio,Benincori, Tiziana,Raimondi, Laura Maria,Rossi, Sergio
, p. 535 - 546 (2020/03/27)
This account summarizes the development of new biheteroaromatic chiral bisphosphine oxides. 3,3′-Bithiophene-based phosphine oxides (BITIOPOs) have been successfully used as organocatalysts to promote Lewis base catalyzed, Lewis acid mediated stereoselective transformations. These highly electron-rich compounds, in combination with trichorosilyl derivatives (allyltrichlorosilane and silicon tetrachloride), generate hypervalent silicon species that act as chiral Lewis acids in highly diastereo- and enantioselective organic reactions. Several relevant examples related to these applications are discussed in detail. 1 Introduction 2 The BITIOPO Family 3 Enantioselective Opening of Epoxides 4 Enantioselective Allylation of Aldehydes 5 Stereoselective Direct (Double) Aldol-Type Reaction with Ketones 6 Stereoselective Direct Aldol-Type Reaction with Ester Derivatives 7 Conclusions.
A method for preparing chiral ring phosphoric acid (by machine translation)
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Paragraph 0048, (2017/03/18)
The invention discloses a method for preparing chiral ring of phosphoric acid, the method comprises the following steps: a Isobutyraldehyde, aromatic aldehyde under the condition of chiral catalyst to catalyze the reaction generating chiral 3-aryl-3-hydroxy -2,2-dimethyl-propionaldehyde; chiral b 3-aryl-3-hydroxy -2,2-dimethyl propionic aldehyde reduction to obtain chiral 1-aryl -2,2-dimethyl -1,3-propylene glycol; c in methylene chloride under the conditions of reaction with phosphorus oxychloride to obtain chiral 4-aryl-2-chloro -5,5-dimethyl-2-oxo -1, 3, 2-dioxo-phosphorus heterocycle hexane chloride; in d hydrolysis under alkaline conditions, dyeworks generating chiral ring phosphoric acid. The high optical purity of the target product, the operation is simple, low cost, high yield, less pollution, belonging to the field of organic synthesis. (by machine translation)
Optical enrichment in enzyme-catalyzed resolution of 1-aryl-2,2-dimethyl-1,3-propanediols
Mukherjee, Chandrani,Mohapatra, Prabhu P.,Youssef, Dani,Jha, Amitabh
, p. 1 - 6 (2017/01/10)
Novozym 435 efficiently catalyzed the chemo-, regio-, and enantioselective transesterification of 1-aryl-2,2-dimethyl-1,3-propanediols in different organic solvents with vinyl acetate as the acetyl donor at room temperature. This enzyme-catalyzed chemical
Biheteroaromatic diphosphine oxides-catalyzed stereoselective direct aldol reactions
Rossi, Sergio,Benaglia, Maurizio,Genoni, Andrea,Benincori, Tiziana,Celentano, Giuseppe
supporting information; experimental part, p. 158 - 166 (2011/02/27)
A highly stereoselective direct aldol condensation of ketones to aromatic aldehydes was realized; the trichlorosilyl enolether generated in situ in the presence of tetrachlorosilane is activated by catalytic amounts of an enantiomerically pure biheteroaromatic phosphine oxide to react with aldehydes, coordinated as well as activated by the chiral cationic hypervalent silicon species. This Lewis acid-mediated Lewis base-catalyzed transformation allowed, starting from two carbonyl compounds, to directly synthesize β-hydroxy ketones generally with high anti stereoselectivity and up to 93% ee for the anti isomer.
Novel enantioselective direct aldol-type reaction promoted by a chiral phosphine oxide as an organocatalyst
Kotani, Shunsuke,Shimoda, Yasushi,Sugiura, Masaharu,Nakajima, Makoto
supporting information; experimental part, p. 4602 - 4605 (2009/10/26)
Chiral phosphine oxide successfully catalyzed the direct aldol-type reactions of cyclohexanone derivatives and benzaldehyde derivatives in high stereoselectivities. The reaction mechanism involves the in situ formation of trichlorosilyl enol ethers. The present reaction could be extended to the cross-aldol reactions between two aldehydes.
(S)-2H-2-oxo-5,5-dimethyl-4(R)-phenyl-1,3,2-dioxaphosphorinane, a New Reagent for the Enantiomeric Excess Determination of Unprotected Amino Acids using 31P NMR
Hulst, Ron,Zijlstra, Robert W. J.,Vries, N. Koen de,Feringa, Ben L.
, p. 1701 - 1710 (2007/10/02)
Diastereomeric amide derivatives of title phosphorinane 2 and unprotected amino acids are easily prepared in aqueous solutions, showing well separated signals in the 31P NMR spectra allowing accurate e.e. determination.
1-Aryl-2,2-dimethyl-1,3-propanediols as chiral auxiliares. Acetal formation with α,β-unsaturated aldehydes and analysis of the stereochemistry of cyclopropanation
Ebens, Rijko,Kellogg, Richard M.
, p. 552 - 560 (2007/10/02)
Optically pure 1-aryl- (phenyl and 2-chlorophenyl) 1,3-propanediols, 1a and 1b, condense smoothly with aldehydes to provide the corresponding cyclic acetals 3.Except in cases that the aldehyde is substituted at the α-carbon atom, a single product is obtai
Enantioselective Syntheses of Aldols and Homoallylic Alcohols from 1,3-Dioxolan-4-ones Using Mandelic Acid as Chiral Auxiliary
Mashraqui, Sabir H.,Kellogg, Richard M.
, p. 2513 - 2516 (2007/10/02)
The 1,3-dioxolan-4-ones obtained by condensation of (S)-(+)- or (R)-(-)-mandelic acid with aldehydes and ketones react under electrophilic conditions cleanly and with reasonable diastereoselectivities with enol silyl ethers or allylsilanes.The chiral auxi
