ISSN:
0947-3440
Keywords:
Domino reaction
;
Functionalized cyclopentanes, -hexanes and -heptanes
;
Tetrahydrofurans
;
Oxetanes
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
1,3-Functionalized cyclopentanes, -hexanes and -heptanes are obtained by addition of lithiated silyldithioacetals 7 to epoxyhomoallyl tosylates 4-6, The reaction involves a cascade of epoxide ring opening, of Brook 1,4-rearrangement and tosylate substitution. The method is particularly suitable for the preparation of cyclopentanes, whereas cyclohexanes and -heptanes are formed in yields only up to 49%. Use of enantiomerically pure epoxides provides optically active cyclopentanes (S)-10b, d, 11a as well as oxetanes (S)-14a, b. Hydrolysis of the dithioacetal function leads to the corresponding ketones 12, Cyclization of epoxide 24b gives an anellated cyclopentane 26, the configuration of which was established by X-ray structural analysis of dinitrobenzoate 27. Use of epoxide 29b provides the anellated tetrahydrofuran 30.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199619961115
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