100190-37-2Relevant academic research and scientific papers
Total syntheses of (+)-adunctins C and D: Assignment of their absolute configurations
Luo, Gan,Peng, Yu,Wang, Ya-Wen,Xiao, Jian,Zhao, Jun
supporting information, p. 9840 - 9843 (2021/12/07)
The first total synthesis of (+)-adunctin C (ent-1) and (+)-adunctin D (2), two monoterpene-substitued dihydrochalcones isolated from Piper aduncum (Piperaceae), was achieved. A regioselective oxidative [3 + 2] cycloaddition of acylphloroglucinol with (-)-β-phellandrene was developed to construct their unique spirobenzofuran skeleton. The absolute configurations of natural adunctins 1 and 2 were thus assigned through these endeavors. This journal is
Optimisation of a lithium magnesiate for use in the non-cryogenic asymmetric deprotonation of prochiral ketones
Francos, Javier,Zaragoza-Calero, Silvia,O'Hara, Charles T.
, p. 1408 - 1412 (2014/01/06)
A study has been conducted to determine whether lithium magnesiates are feasible candidates for the enantioselective deprotonation of 4-alkylcyclohexanones. The commercially available chiral amine (+)-bis[(R)-1-phenylethyl]amine (2-H) was utilised to indu
Enantioselective desymmetrization of prochiral ketones via an organocatalytic deprotonation process
Claraz, Aurelie,Oudeyer, Sylvain,Levacher, Vincent
, p. 764 - 768 (2013/07/25)
The first desymmetrization of 4-substituted cyclohexanones by organocatalytic asymmetric deprotonation at low catalyst loading is reported. The combination of N,O-bis(trimethylsilyl)acetamide (BSA) and chiral quaternary ammonium aryloxide salts has been u
New potentially dhelating chiral magnesium amide bases for use in enantioselective deprotonation reactions
Kerr, William J.,Middleditch, Michael,Watson, Allan J. B.
supporting information; experimental part, p. 177 - 180 (2011/03/22)
A series of chiral secondary amines, incorporating a five- or six-membered heterocycle, were synthesised and used to prepare novel chiral magnesium bisamide reagents. These amide bases were subsequently applied within asymmetric deprotonation reactions to
Towards energetically viable asymmetric deprotonations: Selectivity at more elevated temperatures with C2-symmetric magnesium bisamides
Bennie, Linsey S.,Kerr, William J.,Middleditch, Michael,Watson, Allan J. B.
supporting information; experimental part, p. 2264 - 2266 (2011/04/12)
A novel chiral magnesium bisamide has enabled the development of effective asymmetric deprotonation protocols at substantially more elevated temperatures. This new, structurally simple, C2-symmetric magnesium complex displays excellent levels o
Chiral and achiral lithium amides having a fluorous ponytail: Preparation and evaluation as a recycling reagent for lithium enolate generation
Matsubara, Hiroshi,Maeda, Louis,Sugiyama, Hiroyuki,Ryu, Ilhyong
, p. 2901 - 2912 (2008/03/13)
Diisopropylamine derivatives bearing a perfluoroalkyl chain were prepared and converted to the corresponding lithium amides by treatment with n-butyllithium. The fluorous lithium amides reacted with ketones to efficiently produce lithium enolates. Asymmetric deprotonation of prochiral ketones was also studied using lithium amides derived from chiral fluorous amines, which gave optical yields comparable with the parent nonfluorous chiral lithium amides. These reusable fluorous amines can be easily recovered by liquid-liquid extraction or chromatographic separation. Georg Thieme Verlag Stuttgart.
Application of polydentate chiral amines within magnesium-mediated asymmetric deprotonation reactions
Bassindale, Martin J.,Crawford, James J.,Henderson, Kenneth W.,Kerr, William J.
, p. 4175 - 4179 (2007/10/03)
A set of polydentate secondary amines, each containing two stereogenic centres, were prepared. These were subsequently utilised in magnesium-mediated asymmetric deprotonation reactions and excellent enantiomeric ratios were obtained (up to 94:6 er). Furth
Novel enantiomerically pure heteroleptic magnesium complexes for use in enantioselective deprotonation reactions
Carswell, Emma L.,Hayes, Douglas,Henderson, Kenneth W.,Kerr, William J.,Russell, Claire J.
, p. 1017 - 1021 (2007/10/03)
Two classes of heteroleptic magnesium complexes, alkylmagnesium amides RMgNR2 and aryloxymagnesium amides ROMgNR2, have been prepared and subsequently shown to be efficient bases in the enantioselective deprotonation of substituted c
Magnesium amide base-mediated enantioselective deprotonation processes
Henderson, Kenneth W,Kerr, William J,Moir, Jennifer H
, p. 4573 - 4587 (2007/10/03)
A novel homochiral magnesium bisamide has been readily prepared and, following careful optimisation, this species has been shown to react efficiently with a series of prochiral 4-substituted cyclohexanones in the presence of TMSCl to give the corresponding silyl enol ethers in enantiomeric ratios of up to 95:5. Additionally, the same chiral base system has been shown to be highly effective in the desymmetrisation of cis-2,6-disubstituted cyclohexanones, providing excellent levels of both conversion and enantioselection (up to >99.5:0.5 er). Furthermore, the magnesium bisamide has also been shown to mediate a kinetic resolution process with the corresponding trans-disubstituted substrates, allowing access to enantioenriched enol ethers and ketones.
Stereoselective reactions. XXXIV. Enantioselective deprotonation of prochiral 4-substituted cyclohexanones using chiral bidentate lithium amides having a bulky group instead of a phenyl group on the chiral carbon
Toriyama,Sugasawa,Motohashi,Tokutake,Koga
, p. 468 - 472 (2007/10/03)
Using chiral bidentate lithium amides having a bulky group instead of a phenyl group on the chiral carbon, enantioselective deprotonation of prochiral 4-substituted cyclohexanones in the presence of excess trimethylsilyl chloride was examined in THF in th
