One-pot synthesis of functionalized β-amino sulfides/β-amino selenides via ring opening of cyclic sulfamidates

Abstract

Ring opening of cyclic sulfamidates has been achieved using dichalcogenides in the presence of rongalite to furnish functionalized β-amino chalcogenides.

Nickel-Catalyzed Asymmetric Hydrogenation of Cyclic Sulfamidate Imines: Efficient Synthesis of Chiral Cyclic Sulfamidates

“…Efficient synthesis of chiral cyclic sulfamidates has attracted great attention in the past decades, owing to their versatilities working as valuable intermediates for the construction of some important organic compounds and bioactive molecules (Aguilera and Fernandez-Mayoralas, 1996, Williams et al., 2003, Bower et al., 2004, Bower et al., 2007a, Bower et al., 2007b, Bower et al., 2007c, Bower et al., 2010, Jamieson et al., 2009, Lorion et al., 2010, Megia-Fernandez et al., 2011, Boulton et al., 1999, Wei and Lubell, 2000, Espino et al., 2001, Cohen and Halcomb, 2001, Cohen and Halcomb, 2002, Atfani et al., 2001, Nicolaou et al., 2002, Meléndez and Lubell, 2003, Ni et al., 2007, Rönnholm et al., 2007, Baig et al., 2010, Baig et al., 2011, Venkateswarlu et al., 2014, Albu et al., 2016, Su et al., 2016, Chen et al., 2014, Kong et al., 2015, Liu et al., 2017, Wu et al., 2018). For example, ring-opening reactions of chiral cyclic sulfamidates can offer convenient and efficient access to chiral amines, amino alcohols, amino acids, and their derivatives (Boulton et al., 1999, Wei and Lubell, 2000, Espino et al., 2001, Cohen and Halcomb, 2001, Cohen and Halcomb, 2002, Atfani et al., 2001, Nicolaou et al., 2002, Meléndez and Lubell, 2003, Ni et al., 2007, Rönnholm et al., 2007, Baig et al., 2010, Baig et al., 2011, Venkateswarlu et al., 2014, Albu et al., 2016, Su et al., 2016, Chen et al., 2014, Kong et al., 2015, Liu et al., 2017, Wu et al., 2018). So far the asymmetric catalytic synthetic methods of chiral cyclic sulfamidates were mainly focused on transition metal-catalyzed asymmetric intramolecular amidation of sulfamate esters (Liang et al., 2002, Liang et al., 2004, Fruit and Mueller, 2004, Zhang et al., 2005, Zalatan and Du Bois, 2008, Lin et al., 2008, Ichinose et al., 2011), additions of organoboron reagents to cyclic imines (Chen et al., 2014, Chen ...…”

Ring opening reactions of heterocycles with selenium and tellurium nucleophiles

“…Other five membered heterocycles such as 5-membered cyclic sulfamidates 89 were found to behave as versatile electrophiles towards phenyl selenolate, generated by reaction of diphenyl diselenide with rongalite/K 2 CO 3 , to give enantiopure β-amino phenyl selenides 7 in high yields (Scheme 58). 80…”

Gold(I)‐Catalyzed Intramolecular Dehydrative Amination of Sulfamate Esters Tethered to Allylic Alcohols: A Strategy for the Synthesis of Cyclic Sulfamidates

“…Notably, the reactivity of 1,2‐ and 1,3‐cyclic sulfamidates is comparable to that of activated aziridines and azetidines, respectively [2] . Thus, various nucleophiles readily attack exclusively at the O ‐bearing carbon center in a stereospecific (S N 2) manner to deliver an N ‐sulfate intermediate [3] further hydrolyzed under acidic conditions to the final functionalized amine (Nu − =CN − , F − , N 3 − , RS − , RO − ), [4] functionalized lactam (Nu − =EtO 2 CHC − FG), [2] or functionalized piperazine/thiomorpholine (Nu − =EtO 2 CCH 2 X − ) [5] (Scheme 1).…”