ISSN:
0947-3440
Keywords:
Tetrahydrofurans, formation of
;
Cyclization, stereocontrolled
;
Vinylsilanes
;
Allylsilanes
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Silyl-substituted 4-alken-1-ols cyclize in the presence of a wide range of electrophilic reagents to give substituted tetra-hydrofurans. The silyl group accelerates ring closure by its β-effect and its position determines the efficiency of stereo-control. Thus, a vinylic silyl group as in 1, 3-9 gives mixtures of 2,5-disubstituted tetrahydrofurans 2, 10-21, favoring formation of the trans isomer. In contrast, an allylic silyl group as in 28-30 exerts a high degree of stereocontrol, generally affording 2,3-trans-disubstituted tetrahydrofurans 31-36.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199519950369
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