2431-91-6Relevant academic research and scientific papers
Hindered organoboron groups in organic chemistry. 28 The solvolyses of bis(2,6-dimethyl-4-methoxyphenyl)organylboranes, (DMP)2BR
Pelter, Andrew,Drake, Robert
, p. 13801 - 13828 (1994)
Mineral acid catalysed methanolysis of bis (2,6-dimethyl-4-methoxyphenyl)organylboranes (DMP)2BR, (1), is much faster than that of the corresponding dimesitylorganylboranes, MeS2BR. This allows for the release of organyl groups from 'overhindred' boranes. It also provides a link between (DMP)2BR, from which α-carbanions can be produced, and RB(OMe)2 which do not yield α-carbanions. Solvolyses can be enhanced by the use of glycol, which renders even acetic acid on effective solvolyses catalyst.
Direct synthesis of anilines and nitrosobenzenes from phenols
St Amant,Frazier,Newmeyer,Fruehauf,Read De Alaniz
supporting information, p. 5520 - 5524 (2016/07/06)
A one-pot synthesis of anilines and nitrosobenzenes from phenols has been developed using an ipso-oxidative aromatic substitution (iSOAr) process. The products are obtained in good yields under mild and metal-free conditions. The leaving group effect on reactions that proceed through mixed quionone monoketals has also been investigated and a predictive model has been established.
Three-component asymmetric catalytic ugi reaction - Concinnity from diversity by substrate-mediated catalyst assembly
Zhao, Wenjun,Huang, Li,Guan, Yong,Wulff, William D.
, p. 3436 - 3441 (2014/04/03)
The first chiral catalyst for the three-component Ugi reaction was identified as a result of a screen of a large set of different BOROX catalysts. The BOROX catalysts were assembled in situ from a chiral biaryl ligand, an amine, water, BH3×SMe2, and an alcohol or phenol. The catalyst screen included 13 different ligands, 12 amines, and 47 alcohols or phenols. The optimal catalyst system (LAP 8-5-47) provided α-amino amides from an aldehyde, a secondary amine, and an isonitrile with excellent asymmetric induction. The catalytically active species is proposed to be an ion pair that consists of the chiral boroxinate anion and an iminium cation. Harmonious arrangement of parts: A screen of BOROX catalysts that were generated in situ from 13 different ligands and 47 alcohols led to the identification of an effective combination for the catalytic asymmetric three-component Ugi reaction. Experimental results suggest that the catalyst is a chiral polyborate anion, which then forms an ion pair with the iminium cation that is generated from aldehyde and secondary amine.
A second-generation total synthesis of (+)-discodermolide: The development of a practical route using solely substrate-based stereocontrol
Paterson, Ian,Delgado, Oscar,Florence, Gordon J.,Lyothier, Isabelle,O'Brien, Matthew,Scott, Jeremy P.,Sereinig, Natascha
, p. 150 - 160 (2007/10/03)
(Chemical Equation Presented). A novel total synthesis of the complex polyketide (+)-discodermolide, a promising anticancer agent of sponge origin, has been completed in 7.8% overall yield over 24 linear steps, with 35 steps altogether. This second-genera
A hierarchy of aryloxide deprotection by boron tribromide
Punna, Sreenivas,Meunier, Stephane,Finn
, p. 2777 - 2779 (2007/10/03)
Aryl propargyl ethers and esters are cleaved selectively in the presence of aryl methyl ethers and esters by boron tribromide in dichloromethane. Under the same conditions, allyl ethers undergo very rapid Claisen rearrangement, and benzyl ethers are also cleaved more rapidly than propargyl. A mechanism involving intramolecular delivery of bromide to the propargyl terminus is proposed.
SYNTHESIS OF DISCODERMOLIDE
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Page 89; 90, (2010/11/30)
The invention relates to a process for preparing discodermolide, for preparing intermediates for the manufacture of discodermolide and discodermolide analogues and to the intermediates obtained during the process. Wherein the process proceeds via a tetrae
STEREOCONTROLLED SYNTHESIS OF BOTH THE ENANTIOMERS OF PHASEIC ACID AND ITS METHYL ESTERS, A PIVOTAL METABOLITE OF ABSCISIC ACID.
Kitahara, Takeshi,Touhara, Kazushige,Watanabe, Hidenori,Mori, Kenji
, p. 6387 - 6400 (2007/10/02)
Both the enantiomers of phaseic acid 2a and its methyl ester 2b were synthesized in highly stereocontrolled manner starting from ethyl (1R,2S)-5,5-ethylenedioxy-2-hydroxycyclohexanocarboxylate 5 of 98.4 percent e.e. 6-Oxabicyclooctenone 16 was empl
