Reagent for protection of diols as their cyclic boronates: J. Am. Chem. Soc., 80, 2443 (1958); Tetrahedron, 25, 477 (1969), which are also useful in GC and GC-MS. This has been utilized to trap cis-diols, in order to prevent over-oxidation during dihydroxylation reactions catalyzed by Osmium(VIII)- oxide: Chem. Lett., 1721 (1988); J. Org. Chem., 63, 7322 (1998). Promotes the ortho-hydroxalkylation of phenols by aldehydes. The cyclic boronate, formed via a [3,3] sigmatropic rearrangement, is the key intermediate: Synthesis, 365 (1979).With citronellal, hexahydrocannabinoids are formed: J. Chem. Soc., Perkin 1, 605 (1992). Acts as a template for Diels-Alder reactions, by forming boronate linkages with a hydroxydiene and a hydroxydienophile: Synthesis 1171 (1991); for Nicolaou's application to synthesis of the CD ring system of taxol, see: J. Chem. Soc., Chem. Commun., 1118 (1992); J. Am. Chem. Soc., 117, 634 (1995). Forms a stable chiral acyloxyborane (CAB) catalyst with tartaric acid derivatives, which catalyze hetero Diels-Alder reactions, e.g. between aldehydes and 1-Methoxy-3-trimethyl-siloxy-1,3-butadiene, to give enantioselectively, dihydro-4-pyrone derivatives: Tetrahedron, 50, 979 (1994). The most widely-used reaction of arylboronic acids is the Pd-catalyzed Suzuki synthesis of unsymmetrical biaryls: Synth. Commun., 11, 513 (1981). For illustrative example, see: Org. Synth., 75, 53 (1997).For a brief feature on uses of this reagent in Organic synthesis, see: Synlett, 2679 (2006).
