Synthesis of substituted Z-styrenes by Hiyama-type coupling of oxasilacycloalkenes: application to the synthesis of a 1-benzoxocane
2017 ◽
Vol 13
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pp. 2122-2127
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Keyword(s):
Several Hiyama cross-coupling reactions of oxasilacycloalkenes and aryl iodides are described that produce trisubstituted Z-styrenes in moderate to excellent yields. Both electron-rich and electron-poor aryl iodides are tolerated in the cross-coupling reaction. The oxasilacycloalkene coupling partners were prepared by ruthenium-catalyzed intramolecular anti-hydrosilylation of alkynols. One of the cross-coupling products was converted to a 1-benzoxocane, albeit in low yield, using an intramolecular Buchwald–Hartwig etherification. The cyclic ether produced contains the carbon skeleton of heliannuol A.
2015 ◽
Vol 13
(47)
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pp. 11432-11437
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2020 ◽
2017 ◽
Vol 15
(27)
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pp. 5805-5810
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2018 ◽
Vol 16
(43)
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pp. 8106-8114
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Keyword(s):