Tartrate-derived (2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenylbutane-2,3-diol has found diverse applications in asymmetric organic synthesis. Among these, its utilization as a protecting group for boronic acids has been investigated extensively. Besides being extraordinarily stable and thus allowing a plethora of transformations, it enables access to various diastereo- and enantiomerically pure organoboron reagents and versatile intermediates in asymmetric synthesis.
New alkenylboronic esters were synthesised from halo-substituted alkenylboronic esters through cross-coupling reactions. Upon Johnson rearrangement, enantiomerically pure allylboronates bearing a stereogenic centre in the position α to the boron moiety were obtained in moderate yield (53 %; 29 % over six steps from the protected propargylic alcohols). The
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.