Palladium-Catalyzed Highly Regio- and Stereoselective Addition of Organoboronic Acids to Allenes in the Presence of AcOH
The Pd0-catalyzed regio- and stereoselective addition of organoboronic acids to allenes leads to stereodefined tri- or tetrasubstituted alkenes. Furthermore, this method shows high substitutent-loading capability and tolerance of various substitutents. A hydropalladation-Suzuki coupling mechanism, which may account for the regio- and stereoselectivity, is proposed.
Probing the mechanism of the palladium-catalyzed addition of organoboronic acids to allenes in the presence of AcOH by ESI-FTMS
Three key intermediates in the palladium-catalyzed reaction of allenes with organoboronic acids in the presence of AcOH have been characterized by high resolution ESI-FT mass spectrometry (see picture). Their observation allows a better understanding of t
Diastereoselective Intramolecular Hydride Transfer Triggered by Electrophilic Halogenation of Aryl Alkenes
Diastereoselective hydride transfer could be triggered by electrophilic halogenation (bromination or fluorination) of homoallylic alcohol O-Bn ethers. The resulting diastereomerically enriched haloalkyl alcohols underwent subsequent intramolecular nucleop
Wang, Bin,Gandamana, Dhika Aditya,León Rayo, David Fabian,Gagosz, Fabien,Chiba, Shunsuke
supporting information
p. 9179 - 9182
(2019/11/14)
DIASTEREOSELECTIVE SYNTHESIS OF HEXAHYDRO-3H-OXAZOLOPYRIDIN-3-ONE DERIVATIVES BY CYCLIZATION OF α-ACYLAMINORADICAL-OLEFIN SYSTEM
The substituent effect in α-acylaminoradical-olefin cyclization was examined.Treatment of 4-phenylthiooxazolidin-2-ones (10a-f) with tri-n-butyltin hydride in the presence of AIBN yielded 6,7-cis-6,8a-trans-6-alkyl-7-arylhexahydrooxazolopyridin-3-ones (11a-f), respectively, with high diastereoselectivity.