ISSN:
0009-2940
Keywords:
γ-Lactone
;
Reduction
;
γ-Lactol
;
Lewis acid
;
Tetrahydrofurans
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A variety of monosubstituted γ-lactols 4-6 were prepared in good yields by DIBAL reduction of the corresponding γ-lactones 1-3. The monophenyl-substituted lactols 4b-6b were transformed into disubstituted tetrahydrofuran derivatives by replacement of the hydroxyl group by the alkyl residue of organometallic compounds used as nucleophiles. The diastereoselectivity of the substitution was found to depend strongly on the substitution pattern of the γ-lactols. For the reaction of the 3- and 4-substituted derivatives 4b and 5b, respectively, good to excellent trans selectivity was observed, while the 5-substituted derivative reacted without any diastereoselectivity. These results were interpreted by means of the Felkin-Anh model.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19951280904
