117780-08-2Relevant articles and documents
Enantioselective Allylation of Indoles: A Surprising Diastereoselectivity
Brauns, Marcus,Breugst, Martin,Mantel, Marvin,Pietruszka, J?rg,Schmauck, Julie,Ullrich, Patrick
, p. 1894 - 1905 (2020)
Herein we show a novel approach toward the allylation of indoles. Thereby, we explore a class of bench-stable allylboronates and fine-tune their reactivity. The allylations of different substituted indoles proceed with negligible diastereo- and excellent enantioselectivities. This surprising selectivity (up to 99:1 er, up to ≈60:40 dr) is rationalized by DFT calculations.
The intramolecular S = O···H-O hydrogen bond in a chiral cyclic sulfite ester: How it affects the reaction behavior and spectral properties
Hu, Xiaoyun,Chen, Dongzhi,Lan, Jirong,Shan, Zixing
, p. 1291 - 1296 (2016)
The intramolecular S = O···H?O hydrogen bond in a chiral cyclic sulfite ester, which affects the reaction behavior and spectral properties considerably, was studied.
DMT [(?)-(2R,3R)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol], a highly efficient host compound for nitroaromatic guests: selectivity, X-ray and thermal analyses
Barton, Benita,Hosten, Eric C.,Pohl, Pieter L.
, p. 329 - 337 (2018)
In this work, we reveal that the compound (?)-(2R,3R)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol (DMT) is a highly efficient host material for nitroaromatics o-nitrotoluene (o-NT), m-nitrotoluene (m-NT), p-nitrotoluene (p-NT) and nitrobenzene (NB). Each of these guests was included with a 2:1 host:guest ratio. The host displayed selectivity for p-NT and NB when these guests were mixed in equimolar proportions with any one of the other guest solvents, and the host recrystallized from this binary mixture. A selectivity order for the host in these conditions was thus noted to be NB ≈ p-NT > o-NT > m-NT. Furthermore, guests were also mixed in non-equimolar proportions and the host behaviour analysed, the results of which were in accordance with observations from the equimolar studies. Additionally, an equimolar quaternary experiment of all four guests provided a somewhat adjusted host selectivity order [p-NT (39.9%) > NB (30.2%) > m-NT (17.1%) > o-NT (12.8%)]. Single crystal diffraction analyses of all four complexes showed the crystals to share the same host packing, and comparable host–guest interactions were observed in each. However, thermal analyses, both DSC and TG, showed that the preferred guests p-NT and NB formed complexes with increased relative thermal stabilities, and this observation correlated with the selective behaviour of the host in competition experiments.
Enantioselective Allylation of Cyclic and In Situ Formed N-Unsubstituted Imines with Tetraol-Protected Allylboronates
Ullrich, Patrick,Schlamkow, Max A.,Choi, Ching-Yi,Kerkenpa?, Hannah,Hen?en, Birgit,Pietruszka, J?rg
supporting information, p. 6254 - 6257 (2021/11/03)
Tetraol-protected α-chiral allylboronates are utilized in diastereo- and enantioselective transformations of cyclic imines (up to 98 %, d.r. 97 : 3, e.r. 99 : 1). An application to in situ formed N-unsubstituted imines gives in a consecutive one-pot sequence selective access to all four stereoisomers of the homoallylamine within minutes (up to 88 %, d.r. 81 : 19, e.r. 99 : 1). These results underline the usability, tuneability and stability of tetraol-based allylboronates.
Chiral bicyclo[4.4.0]diboronic acid, preparation method and application thereof
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Paragraph 0027; 0028, (2019/05/16)
Belonging to the chemical field of preparation of chiral compounds, the invention in particular relates to a chiral bicyclo[4.4.0]diboronic acid, a preparation method and application thereof. The method starts from chiral 1, 1, 4, 4-tetraarylbutantetraol,
