Allylation of Aldehyde and Imine Substrates with in situ Generated Allylboronates — A Simple Route to Enantioenriched Homoallyl Alcohols.

Abstract

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Diboron(4) Compounds: From Structural Curiosity to Synthetic Workhorse

“…708 The reaction is, nonetheless, synthetically useful, as the addition of an aldehyde or imine to the reaction mixture results in near quantitative yields of the allylboration product and no allyl−allyl coupling, as the borylation product is consumed as it is generated. 709 The use of a chiral diboron source allowed for moderate enantioselectivity, 710 while a more recent publication reported the use of zerovalent nickel or palladium(II) catalysts in the same reaction. 711 Borylation of oxo-2-alkenyl acetates resulted in the generation of oxo-2-alkenyl boranes, which can undergo an intramolecular cyclization reaction (Scheme 89b).…”