Five-membered cyclic sulfamidate imines: versatile scaffolds for organic synthesis

Abstract

In recent years, five-membered ring cyclic sulfamidate imines (5H-1,2,3-oxathiazole 2,2-dioxides) have received increasing attention as useful precursors for the stereoselective synthesis of many valuable heterocycles. Bearing a reactive N-sulfonyl imine...

Catalyst-Free α-Allylation of Dihydroisoquinolines with Morita–Baylis–Hillman Carbonates and Its Applications in the Construction of Benzo[a]quinolizidines

“…Besides, the electron-withdrawing CN bond also slightly increased the acidity of α-C­(sp 3 )–H protons of alkyl ketimines (e.g., 1-alkyl-3,4-dihydroquinolines), making them behave as potential carbonucleophiles to react with different types of electrophiles . However, due to the high p K a value, the research on the functionalization at the α-C­(sp 3 ) position mainly focused on several reactive ketimines, such as N -sulfonyl ketimines, which bear an electron-withdrawing sulfonyl group on the imine nitrogen atom . In contrast, direct α-C­(sp 3 )–H functionalization of common N -alkyl cyclic ketimines like 1-alkyl-3,4-dihydroisoquinolines is still less explored …”

Palladium-catalysed enantio- and regioselective (3 + 2) cycloaddition reactions of sulfamidate imine-derived 1-azadienes towards spirocyclic cyclopentanes

“…2b). 57,58 Such (3 + 2) cycloadditions would proceed via a non-aromatic intermediate II, where attack by the nitrogen on the pendant p-allyl palladium complex would be unlikely as it would result in a strained bicyclic product. Furthermore, in contrast to BDA cycloaddition products, the oxygen substituent in the SDA-derived cyclopentanes would not be attached to an aromatic ring.…”

Kukhtin–Ramirez-Reaction-Inspired Deprotection of Sulfamidates for the Synthesis of Amino Sugars

“…This significance has inspired tremendous efforts to devise elegant synthetic methods for the construction of amino alcohols [9][10][11][12][13][14][15]. Among them, the utility of sulfamate esters [16][17][18][19][20][21] as precursors of amino groups to form cyclic sulfamidate [22][23][24][25] via substitution [26,27], condensation [28][29][30], C-H amination [31][32][33][34], C-H aziridination [35], etc. [36][37][38], has been well established.…”