Cyclic Sulfamidate Imines Research Articles

Entry to Tertiary Carbinamines Bearing a gem-Diaryl Group by Copper-Catalyzed Grignard Addition to Cyclic Sulfamidate Imines.

We report a convenient access to tertiary carbinamines bearing a gem-diaryl group by Cu-catalyzed aryl Grignard addition to cyclic sulfamidate imines and sulfamide imines. The synthesis of hetero-functionalized 1,2-ethylene derivatives by ring-opening of the resulting sulfamidates is also described.

L-Proline catalyzed highly efficient synthesis of Z-5-alkylidene cyclic sulfamidate imines: an easy access to 5-alkyl-substituted cyclic sulfamidate imines

A very simple, mild and robust method for the synthesis of exclusively Z-trisubstituted 5-alkyliden cyclic sulfamidate imines via a condensation reaction of 4-aryl-5H-1,2,3-oxathiazole-2,2-dioxides with aldehydes using L-proline as an organocatalyst at room temperature is reported for the first time. In addition, the synthesis of 5-alkyl substituted cyclic sulfamidate imines, trans-β-amino-α-azido/triazole and 2-hydroxy-4-triazole-5-phenylpyrrolidine derivatives have been developed through this methodology.

Dynamic kinetic resolution in the stereoselective synthesis of 4,5-diaryl cyclic sulfamidates by using chiral rhodium-catalyzed asymmetric transfer hydrogenation

The dynamic kinetic resolution of 4,5-diaryl cyclic sulfamidate imines was achieved via asymmetric transfer hydrogenation using a HCO(2)H/Et(3)N mixture as the hydrogen source and chiral Rh catalysts (R,R)- or (S,S)-RhCl(TsDPEN)Cp* affording the corresponding cyclic sulfamidates in good yields with up to >20 : 1 dr and up to >99% ee.

ChemInform Abstract: Grignard Additions to Cyclic Sulfamidate Imines: Synthesis of N‐Substituted Quaternary Sulfamidate Building Blocks.

AbstractA simple method is developed for the addition of Grignard reagents (in either Et2O or THF) to cyclic sulfamidate imines to give 4‐disubstituted derivatives.

Enantioselective Synthesis of Cyclic Sulfamidates by Using Chiral Rhodium-Catalyzed Asymmetric Transfer Hydrogenation

Asymmetric transfer hydrogenation (ATH) of cyclic sulfamidate imines 4 and 9, using a HCO(2)H/Et(3)N mixture as the hydrogen source and well-defined chiral Rh catalysts (S,S)- or (R,R)-2, Cp*RhCl(TsDPEN), effectively produces the corresponding cyclic sulfamidates with excellent yields and enantioselectivities at room temperature within 0.5 h. ATH of 4,5-disubstituted imines 9, having preexisting stereogenic centers, is shown to take place with dynamic kinetic resolution.

Grignard Additions to Cyclic Sulfamidate Imines: Synthesis of N-Substituted Quaternary Sulfamidate Building Blocks

The addition of Grignard reagents to cyclic sulfamidate imines has been developed as a facile method for the synthesis of N-substituted quaternary sulfamidates. By way of ring opening with an appropriate nucleophile, versatile synthons for 1,2-amino alcohols, 1,2-diamines, and β-amino acids are produced.