Synthesis of cyclic alkenyl dimethylsiloxanes from alkynyl benzyldimethylsilanes and application in polyene synthesis

Synthesis of cyclic alkenyl dimethylsiloxanes from alkynyl benzyldimethylsilanes and application in polyene synthesis

Cyclic dimethylalkenylsiloxanes, useful motifs for (Z)-selective Hiyama cross-coupling, are accessed from alkynyl benzyldimethylsilanes featuring adjacent allylic or homoallylic oxygen substituents by semihydrogenation/debenzylation/cyclization. While formation of 5- and 6-membered rings can be achi...

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מידע ביבליוגרפי
Main Authors: Gudmundsson, HG, Kuper, CJ, Cornut, D, Urbitsch, F, Elbert, BL, Anderson, EA
פורמט: Journal article
שפה:English
יצא לאור: American Chemical Society 2019
תיאור
סיכום:Cyclic dimethylalkenylsiloxanes, useful motifs for (Z)-selective Hiyama cross-coupling, are accessed from alkynyl benzyldimethylsilanes featuring adjacent allylic or homoallylic oxygen substituents by semihydrogenation/debenzylation/cyclization. While formation of 5- and 6-membered rings can be achieved from the free alcohols using fluoride or silanolate, allylic acetate precursors to 5-membered rings display distinct modes of activation. The utility of these compounds is demonstrated through the preparation of a variety of (Z)-alkene-containing polyenes and application to a concise total synthesis of leukotriene B3.

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