Recent progress in asymmetric synthesis of aminophosphonic acids mediated by chiral sulfinyl auxiliary

2017 ◽  
Vol 89 (3) ◽  
pp. 357-365 ◽  
Author(s):  
Marian Mikołajczyk ◽  
Piotr Łyżwa
Keyword(s):  
Asymmetric Synthesis ◽  
Recent Progress ◽  
Asymmetric Induction ◽  
Enantiomerically Pure ◽  
Aminophosphonic Acids

AbstractThis account outlines the recent results on our strategy of the diastereoselective asymmetric synthesis of aminophosphonic acids (APs) using enantiomeric sulfinimines as chirality inducing reagents. Three important topics are discussed: (a) application of a double asymmetric induction in the synthesis of enantiomerically pure APs; (b) development of a general approach to the synthesis of γ-aminophosphonic acids (γ-APs) and (c) the use enantiomeric N-(p-tolylsulfinyl)cinnamaldimines in the synthesis of diverse α- and β-aminophosphonic acids (AP3, AP4) including the first synthesis of (R)-phosphoemeriamine.

Indium Bromide-catalyzed Unprecedented Hydrogenolysis: A Novel One-Pot Synthesis of Per-O-Acetylated β-carboxymethyl O and S-glycosides

2020 ◽  
Vol 24 (8) ◽  
pp. 900-908
Author(s):  
Ram Naresh Yadav ◽  
Amrendra K Singh ◽  
Bimal Banik
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Auxiliary ◽  
Bioactive Molecules ◽  
One Pot ◽  
Enantiomerically Pure ◽  
Stereoselective Glycosylation ◽  
One Pot Synthesis ◽  
Wide Range

Numerous O (oxa)- and S (thia)-glycosyl esters and their analogous glycosyl acids have been accomplished through stereoselective glycosylation of various peracetylated bromo sugar with benzyl glycolate using InBr3 as a glycosyl promotor followed by in situ hydrogenolysis of resulting glycosyl ester. A tandem glycosylating and hydrogenolytic activity of InBr3 has been successfully investigated in a one-pot procedure. The resulting synthetically valuable and virtually unexplored class of β-CMGL (glycosyl acids) could serve as an excellent potential chiral auxiliary in the asymmetric synthesis of a wide range of enantiomerically pure medicinally prevalent β-lactams and other bioactive molecules of diverse medicinal interest.

P-Chiral 2-{1'-[Butyl(phenyl)phosphanyl]ferrocen-1-yl}-4-isopropyl-4,5-dihydrooxazoles: A Second Chirality Center in Catalytic System

2005 ◽  
Vol 70 (3) ◽  
pp. 361-369 ◽  
Author(s):  
Dušan Drahoňovský ◽  
Petr Štěpnička ◽  
Dalimil Dvořák
Keyword(s):  
Catalytic System ◽  
Asymmetric Induction ◽  
Dimethyl Malonate ◽  
Enantiomerically Pure

P-Chiral (S,RP)-2-{1'-[butyl(phenyl)phosphanyl]ferrocen-1-yl}-4-isopropyl-4,5-dihydrooxazole (6) and (S,SP)-2-{1'-[butyl(phenyl)phosphanyl]ferrocen-1-yl}-4-isopropyl-4,5-dihydrooxazole (7) were prepared by the procedure developed by Jugé, starting from enantiomerically pure (-)- or (+)-ephedrine and dichloro(phenyl)phosphine. Compounds 6 and 7 were examined for asymmetric induction in the Pd-catalyzed reaction of rac-1,3-diphenylallyl acetate with dimethyl malonate. The best results were obtained with 7 (98% ee), while 6 gave 82% ee.

Nucleophilic Additions toN-Glycosylnitrones. Asymmetric Synthesis of ?-Aminophosphonic Acids

1985 ◽  
Vol 68 (6) ◽  
pp. 1730-1747 ◽  
Author(s):  
Rolf Huber ◽  
Andreas Knierzinger ◽  
Jean-Pierre Obrecht ◽  
Andrea Vasella
Keyword(s):  
Asymmetric Synthesis ◽  
Nucleophilic Additions ◽  
Aminophosphonic Acids

Asymmetric synthesis of enantiomerically pure 7-isopropenyl-4a-methyl-3-methyleneoctahydrochromen-2-ones

2007 ◽  
Vol 18 (22) ◽  
pp. 2712-2718 ◽  
Author(s):  
Henryk Krawczyk ◽  
Marcin Śliwiński ◽  
Jacek Kędzia ◽  
Jakub Wojciechowski ◽  
Wojciech M. Wolf
Keyword(s):  
Asymmetric Synthesis ◽  
Enantiomerically Pure
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