Palladium-mediated intramolecular aryl amination on furanose derivatives: an expedient approach to the synthesis of chiral benzoxazocine derivatives and tricyclic nucleosides.
Pd-catalyzed intramolecular arylamination on sugar derivatives has been accomplished by using bulky biaryl phosphine ligands. An application of this methodology on a variety of D-glucose-derived substrates, 2a-f, led to the synthesis of highly functionalized cis-fused tricyclic oxazocines, 3a-e. The products could subsequently be transformed to the optically active benzoxazocine derivative 4 and tricyclic nucleoside 6. This is the first example of the synthesis of eight-membered rings via intramolecular cycloamination of furanose derivatives, which provides a very useful method for the catalytic synthesis of medium-ring heterocycles.
Neogi
Arpita
A
Division of Medicinal Chemistry, Indian Institute of Chemical Biology, 4 Raja S. C. Mullick Road, Kolkata-700032, India.
Majhi
Tirtha Pada
TP
Mukhopadhyay
Ranjan
R
Chattopadhyay
Partha
P
D000586:Amination; D000588:Amines / Q000737:chemistry; D001392:Azocines / Q000138:chemical synthesis* / Q000737:chemistry*; D048588:Benzoxazines / Q000138:chemical synthesis* / Q000737:chemistry; D001966:Bromine / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D000588:Amines; D001392:Azocines; D048588:Benzoxazines; D002241:Carbohydrates; D009705:Nucleosides; D010165:Palladium; D007455:Iodine; D001966:Bromine