Total synthesis of ent-pavettamine

• Memory Zimuwandeyi,
• Manuel A. Fernandes,
• Amanda L. Rousseau and
• Moira L. Bode

Beilstein J. Org. Chem. 2021, 17, 1440–1446, doi:10.3762/bjoc.17.99

• steps. As before, (S)-malic acid (3) was chosen as the starting material because its inherent chirality reduced the complexity of the synthetic process. Given the fact that the target molecule has C2 symmetry, it was prudent that a synthetic route starting from a common C5 subunit be chosen, with

Synthetic approaches to bowl-shaped π-conjugated sumanene and its congeners

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 2212–2259, doi:10.3762/bjoc.16.186

• et al. [13], this field of research is continuously booming because of the developments of advanced synthetic organic tools [14][15][16]. Among the PAHs, the buckybowls are of significant importance not only because of the presence of unique inherent chirality (bowl-chirality) originating either from

Attempted synthesis of a meta-metalated calix[4]arene

• Christopher D. Jurisch and
• Gareth E. Arnott

Beilstein J. Org. Chem. 2019, 15, 1996–2002, doi:10.3762/bjoc.15.195

• yielding transformations to azide and 1,2,3-triazole derivatives which may have application in other areas of research. Keywords: calixarene; inherent chirality; mesoionic carbene; mononitration; ruthenacycle; Introduction Calix[4]arenes are a class of diverse macrocyclic compounds which have been the

• whose chiral nature is a result of selective substitution on the calix[4]arene by various functional groups [9]. In particular, we have focused on the less-studied meta-substituted derivatives [10] whose inherent chirality is more commonly introduced by a suitable directing group [11][12][13][14][15

• potential implications for asymmetric catalysis, due to the inherent chirality of the calix[4]arene, coupled with the point chirality from, for example, a tetrahedral ruthenium center. We therefore decided to apply the methods reported by Albrecht to a calix[4]arene system in order to prove this theory

Recent applications of chiral calixarenes in asymmetric catalysis

• Mustafa Durmaz,
• Erkan Halay and
• Selahattin Bozkurt

Beilstein J. Org. Chem. 2018, 14, 1389–1412, doi:10.3762/bjoc.14.117

• ][14][15][16][17][18][19][20][21]. In general, chirality can be introduced into the calixarene platform either by incorporation of a chiral group or by asymmetric placement of achiral substituents, creating chirality associated with form. This is termed inherent chirality [22]. Although chiral

• selectivity was the chiral oxazoline unit and not the inherent chirality of calixarene skeleton. Asymmetric hydrogenation Starting with distally O-dialkylated calixarene precursors, a series of BINOL-derived calix[4]arene-diphosphite ligands 40a–g were synthesized by Liu and Sandoval through phosphorylation

• the inherent chirality of calix[4]arene for α-chloroacetophenone and ortho-chloroacetophenone. The results clearly showed the effect of both denticity of ketone reactant and cooperativity between normal and inherent chirality on the selectivity. More recently, Al(III)–calix[4]arene complexes 116a–c

Polarization spectroscopy methods in the determination of interactions of small molecules with nucleic acids – tutorial

• Tamara Šmidlehner,
• Ivo Piantanida and
• Gennaro Pescitelli

Beilstein J. Org. Chem. 2018, 14, 84–105, doi:10.3762/bjoc.14.5

• (see chapter 2.3., characterization), the difference in the ECD spectrum caused by ligand binding is obtained by subtracting the intrinsic spectrum. However, it should be taken into account that the observed change in the ECD spectrum can have several origins: a) a change of the ligand’s inherent

• chirality due to the structural changes caused by binding; b) an induced (I)CD as a result of ligand insertion into chiral binding sites; c) exciton coupling between multiple aggregated ligand molecules. The appearance of one or more isodichroic points (the CD equivalent of isosbestic points) during ECD

Inclusion complexes of β-cyclodextrin with tricyclic drugs: an X-ray diffraction, NMR and molecular dynamics study

• Franca Castiglione,
• Fabio Ganazzoli,
• Luciana Malpezzi,
• Andrea Mele,
• Walter Panzeri and
• Giuseppina Raffaini

Beilstein J. Org. Chem. 2017, 13, 714–719, doi:10.3762/bjoc.13.70

• compound 1. Compounds 1 and 2 are not planar and the exocyclic double bond prevents the free rotation of the side chain with respect to the ring system. Consequently, 1 and 2 show inherent chirality [9] as lacking of symmetry elements. The main purpose of the work is the comparison of the structural

Inherently chiral calix[4]arenes via oxazoline directed ortholithiation: synthesis and probe of chiral space

• Simon A. Herbert,
• Laura J. van Laeren,
• Dominic C. Castell and
• Gareth E. Arnott

Beilstein J. Org. Chem. 2014, 10, 2751–2755, doi:10.3762/bjoc.10.291

• ) as our means of probing the inherent chirality of our ligands. For comparison we also synthesised planar ligands 10–12 using conventional methods (see Supporting Information File 1). The catalytic runs were conducted under the identical conditions reported by Dai (for comparison purposes) and are

• due to the point chirality of the oxazoline and not the inherent chirality of the calixarene. Since these results are entirely consistent with those of the planar chiral ferrocene system reported by Dai et al., we believe future ligand design may better exploit the inherently chiral calix[4]arene

• inherent chirality on the calix[4]arenes can be also be used to drive asymmetric transformations/reactions. Experimental See Supporting Information File 1. N,S Ligands. Synthesis of inherently chiral calix[4]arenes. Synthesis of tert-butyloxazoline calix[4]arenes. Tsuji–Trost reaction. Results of

Benzyne arylation of oxathiane glycosyl donors

• Martin A. Fascione and
• W. Bruce Turnbull

Beilstein J. Org. Chem. 2010, 6, No. 19, doi:10.3762/bjoc.6.19

• utilising the inherent chirality of the sugar to determine the stereochemistry of the key benzylic centre in the chiral auxiliary, and also facilitates regioselective attachment of the auxiliary group to O-2. The benzylated oxathiane ether 18 also afforded a glycosyl acetate 25 in 57% yield but on this

Novel banana-discotic hybrid architectures

• Hari Krishna Bisoyi,
• H. T. Srinivasa and
• Sandeep Kumar

Beilstein J. Org. Chem. 2009, 5, No. 52, doi:10.3762/bjoc.5.52

• properties such as ferroelectric or anti-ferroelectric switching [1][2][3][4][5][6][7]. The occurrence of superstructural chirality in the mesophase of bent-core compounds with no inherent chirality is not only of fundamental scientific interest but also of industrial application as this chirality can be