ISSN:
1434-193X
Keywords:
Phenylselenenyl sulfate
;
Selenium-catalyzed reactions
;
Stereoselective syntheses
;
Dihydrofurans
;
Tetrahydrofurans
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
-A stereoselective multi-step one-pot procedure for converting 2-methoxycarbonyl-3-alkenols into 3-methoxycarbonyl-2,5-dihydrofurans, using only catalytic amounts of diphenyl diselenide and an excess of ammonium persulfate, has been developed. The erythro alkenols give the trans dihydrofurans, while the threo stereoisomers give the corresponding cisproducts. The configurations of the starting alkenols were deduced from those of the intermediate phenylseleno tetrahydrofurans, which were independently obtained from reactions of the alkenols with stoichiometric amounts of phenylselenenyl sulfate.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
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