458560-71-9Relevant academic research and scientific papers
A [3+3] cyclization strategy for asymmetric synthesis of alkyl substituted piperidine-2-ones using 1,2-cyclic sulfamidates: A formal synthesis of (S)-coniine from l-norvaline
Karanfil, Abdullah,Balta, Berrin,Eskici, Mustafa
, p. 10218 - 10229,12 (2020/09/02)
Regioselective ring-opening reactions of a set of representative 1,2-cyclic sulfamidates with lithium triethylorthopropiolate proceeded efficiently to deliver the corresponding δ-amino-α,β-unsaturated esters after acidic hydrolysis. Hydrogenation of the unsaturated esters and subsequent thermal cyclization afforded the related alkyl substituted piperidine-2-ones. This approach represents a novel [3+3] cyclization strategy for the asymmetric synthesis of alkyl substituted piperidin-2-ones. Efficiency of the cyclization process is illustrated by a formal asymmetric synthesis of (S)-coniine from l-norvaline.
Facile synthesis of β-amino disulfides, cystines, and their direct incorporation into peptides
Nasir Baig,Kanimozhi, Catherine K.,Sudhir, V. Sai,Chandrasekaran, Srinivasan
scheme or table, p. 1227 - 1232 (2009/09/06)
Herein, we report a simple and efficient methodology for the synthesis of β-amino disulfides by regioselective ring opening of sulfamidates with benzyltriethylammonium tetrathiomolybdate [BnNEt3] 2MoS4. Stability and reactivity of different protecting groups under the reaction conditions have been discussed. This methodology has also been extended to serine and threonine derived sulfamidates to furnish cystine and 3,3′-dimethyl cystine derivatives. Georg Thieme Verlag.
Fluoroamines via chiral cyclic sulfamidates
Posakony, Jeffrey J.,Tewson, Timothy J.
, p. 766 - 770 (2007/10/03)
N-benzyl [1,2,3]-oxathiazolidine 2,2-dioxides (cyclic sulfamidates) were synthesized from their corresponding β-amino alcohols and used as substrates in fluorination reactions with tetrabutylammonium fluoride (TBAF). After desulfonation of the intermediates, the N-benzyl fluoroamines were debenzylated by transfer hydrogenolysis with Pd/C to yield (S) and (R)-2-amino-1-fluoropropanes (2b and 3b, respectively, both with 95% ee). The reactions were carried out on multi-gram scale without the need for chromatographic purification of the intermediates. In the presence of carbonate, the (S)- and (R)-N-benzylfluoroamines underwent intramolecular cyclizations in which fluoride was displaced to yield cyclic carbamates 13 and 14.
New routes to N-alkylated cyclic sulfamidates
Posakony, Jeffrey J.,Grierson, John R.,Tewson, Timothy J.
, p. 5164 - 5169 (2007/10/03)
BOC- and dibenzosuberyl-protected chiral and hindered cyclic sulfamidates ([1,2,3]-oxathiazolidine-2,2-dioxides) were synthesized and subsequently deprotected using trifluoroacetic acid. The resulting crystalline sulfamidates were then used in several alk
New carbon-carbon bond forming reactions of cyclic sulfate esters and cyclic sulfamidates
Pound, Melanie K,Davies, Darren L,Pilkington, Melanie,De Pina Vaz Sousa, Maria M,Wallis, John D
, p. 1915 - 1918 (2007/10/03)
Carbon-carbon bonding forming reactions of two cyclic sulfate esters and a cyclic sulfamidate are reported, the former with lithium dianions to give substituted tetrahydrofuran derivatives with displacement of sulfate, and the latter undergoes ring-openin
