Zinc(II) triflate-controlled 1,3-dipolar cycloadditions of C-(2-thiazolyl)nitrones: application to the synthesis of a novel isoxazolidinyl analogue of tiazofurin.
[reaction: see text] The cycloaddition reaction between C-(2-thiazolyl) nitrones and allylic alcohol takes place with complete exo selectivity when the reactions are carried out in the presence of 1 equiv of zinc triflate. The rate of the reaction is increased enormously under microwave irradiation. The use of a chiral dipolarophile allowed application of the methodology to the synthesis of a hitherto unknown enantiomerically pure isoxazolidinyl analogue of the C-nucleoside tiazofurin.
Chiacchio
Ugo
U
Dipartimento di Scienze Chimiche, Università di Catania, Italy.
Rescifina
Antonio
A
Saita
Maria G
MG
Iannazzo
Daniela
D
Romeo
Giovanni
G
Mates
Juan A
JA
Tejero
Tomas
T
Merino
Pedro
P
D000475:Alkenes / Q000737:chemistry; D001391:Azo Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D002942:Circular Dichroism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D010084:Oxidation-Reduction; D020005:Propanols / Q000737:chemistry; D012254:Ribavirin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D017967:Zinc Compounds / Q000737:chemistry*
D000475:Alkenes; D001391:Azo Compounds; D009589:Nitrogen Oxides; D020005:Propanols; D017967:Zinc Compounds; C015388:nitrones; C006463:allyl alcohol; D012254:Ribavirin; C033706:tiazofurin