Asymmetric Synthesis of α-Aminoboronic Acid Derivatives by Copper-Catalyzed Enantioselective Hydroamination
A copper-catalyzed regio- and enantioselective hydroamination of alkenyl dan boronates (dan =1,8-diaminonaphthyl) with hydrosilanes and hydroxylamines proceeds to deliver the chiral α-aminoboronic acids in good yields with high enantiomeric ratios. The ke
Modular Synthesis of a Versatile Double-Allylation Reagent for Complex Diol Synthesis
Double-allylation reagents allow for the construction of highly complex molecules in an expedient fashion. We have developed an efficient, modular, and enantioselective approach towards accessing novel variants of these reagents through Cu/Pd-catalyzed alkenylboration of alkenylboron derivatives. Importantly, we demonstrate novel use of an allylBdan reagent directly in a stereocontrolled allylation without initial deprotection to the boronic ester. These allylation products are employed in a second intermolecular allylation to access complex diol motifs, which has yet to be shown with these types of double-allylation reagents. Overall, the modularity of this approach and the ease in which complex structural motifs can be accessed in a rapid manner signify the importance and utility of this method.
Synthesis of B-protected β-styrylboronic acids via iridium-catalyzed hydroboration of alkynes with 1,8-naphthalenediaminatoborane leading to iterative synthesis of oligo(phenylenevinylene)s
Hydroboration of aromatic and aliphatic alkynes with 1,8- naphthalenediaminatoborane ((dan)BH) proceeded in the presence of [IrCl(cod)]2 complex with a DPPM or DPEphos ligand, affording alkenylboronic acids whose boronyl groups are masked by th
Iwadate, Noriyuki,Suginome, Michinori
supporting information; experimental part
p. 1899 - 1902
(2009/09/30)
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