N?Heterocyclic Carbene?Catalyzed Atroposelective Annulation for Access to Thiazine Derivatives with C?N Axial Chirality

نویسندگان

چکیده

A catalytic atroposelective cycloaddition reaction between thioureas and ynals is developed. This features the first NHC-catalyzed addition of to acetylenic acylazolium intermediates eventually set up C?N axial chirality with excellent optical purities. The obtained axially chiral thiazine derivative products bear multiple functional groups are feasible for further transformations.

برای دانلود باید عضویت طلایی داشته باشید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Supramolecular chirality in crystalline assemblies of bile acids and their derivatives; three-axial, tilt, helical, and bundle chirality.

Steroidal bile acids and their derivatives exhibit characteristic inclusion behaviors in the crystalline state. Their crystals present varied assemblies due to asymmetric molecular structures, which relate to supramolecular properties through cooperative weak interactions. An overview indicates that the steroidal assemblies lie in an intermediate position among various molecules and have hierar...

متن کامل

Light-driven molecular switches with tetrahedral and axial chirality.

Two light-driven molecular switches with tetrahedral and axial chirality were synthesized, which can induce a helical superstructure in an achiral liquid crystal host and dynamically phototune it to achieve reversible reflection color.

متن کامل

Discrimination of hydrogen-bonded complexes with axial chirality

The chiral self-discrimination of twelve molecules showing axial chirality has been studied. They included peroxides, hydrazines, carboxylic acids, amides, and allenes. The homo and heterochiral dimers of the selected compounds, that present two hydrogen bonds, have been studied by means of density functional theory ~B3LYP/6-311G**! and ab initio ~MP2/6-311G** and MP2/6-31111G**! methods. The e...

متن کامل

Induced preference for axial chirality in a triarylmethylium o,o-dimer upon complexation with natural γ-cyclodextrin: strong ECD signaling and fixation of supramolecular chirality to molecular chirality.

The ratio of the easily interconverting rotational isomers of biphenyl-2,2'-diylbis[bis(4-dimethylaminophenyl)methylium] (R)/(S)-1a(2+) can be biased to prefer an R configuration upon 1:1 complexation with γ-cyclodextrin in water. Through the reaction with Na(2)S, the preference of 1a(2+)@γ-CyD for an axial chirality of R can be fixed as the M-helicity of dihydrothiepin 2.

متن کامل

A three-component reaction for rapid access to underexplored 1,3-thiazine-2-thiones.

Driven by the shortage of known effective possibilities for the synthesis of 4-hydroxy-3,4-dihydro-2H-1,3-thiazine-2-thiones on the one hand and the promising potential of these structures as novel drug candidates on the other hand, synthetic access to 4-hydroxy-3,4-dihydro-2H-1,3-thiazine-2-thiones was developed. The desired products could be synthesized effectively and facilely starting from ...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

ژورنال

عنوان ژورنال: Angewandte Chemie

سال: 2021

ISSN: ['1521-3773', '1433-7851', '0570-0833']

DOI: https://doi.org/10.1002/anie.202010606