Yanagi, Tomoyuki published the artcileAsymmetric systematic synthesis, structures, and (chir)optical properties of a series of dihetero[8]helicenes, Safety of ((1S,4R)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonyl chloride, the publication is Chemical Science (2021), 12(8), 2784-2793, database is CAplus and MEDLINE.
A series of dihetero[8]helicenes (P)/(M)/(rac)-I (R = O, S, NH, SO2) have been systematically synthesized in enantiomerically enriched forms by utilizing the characteristic transformations of the organosulfur functionality. The synthetic route begins with assembling a ternaphthyl II common synthetic intermediate from 2-naphthol and 2,7-bis(phenethylsulfinyl)naphthalene through an extended Pummerer reaction followed by facile multi-gram-scale resolution The subsequent cyclization reactions into dioxa- and dithia[8]helicenes (P)/(M)/(rac)-I take place with excellent axial-to-helical chirality conversion. Dithia[8]helicenes (P)/(M)/(rac)-III are further transformed into the nitrogen (P)/(M)/(rac)-I and the carbon analogs (P)/(M)/(rac)-IV and (P)/(M)/(rac)-V by replacing the two endocyclic sulfur atoms via SNAr-based skeletal reconstruction. The efficient systematic synthesis has enabled comprehensive evaluation of phys. properties, which has clarified the effect of the endocyclic atoms on their structures and (chir)optical properties as well as the unexpected conformational stability of the common helical framework.
Chemical Science published new progress about 21286-54-4. 21286-54-4 belongs to chlorides-buliding-blocks, auxiliary class Chiral,Chloride,Sulfonyl chlorides,Aliphatic cyclic hydrocarbon,Ketone, name is ((1S,4R)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonyl chloride, and the molecular formula is C10H15NO, Safety of ((1S,4R)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonyl chloride.
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