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1,2-stereochemical induction in the Pd<sup>II</sup>-catalyzed conjugate addition of boronic acids

AuthorsRoscales, S.; Sánchez, Francisco; Csákÿ, Aurelio G.
Chiral pool
Michael addition
Synthetic methods
Issue Date2015
CitationEuropean Journal of Organic Chemistry 2015: 1754-1763 (2015)
AbstractPalladium(II) catalysis has been used in the substrate-controlled 1,2-chiral induction of the conjugate addition of boronic acids to enantiopure α,β-unsaturated ketones and esters without competition from the Mirozoki-Heck reaction. Bedford's palladacycle was found to control the stereoselectivity without the need for additional chiral ligands. We report that the Pd<sup>II</sup>-catalyzed conjugate addition reaction between boronic acids and acyclic ketones or esters that bear a hydroxyl substituent at their γ-position (glyceraldehyde derivatives) can afford high levels of anti stereoselection, comparable to those reported previously using more expensive Rh<sup>I</sup> catalysts. On the other hand, high levels of syn stereoselectivity were observed with acyclic esters that bear an amino substituent at their γ-position (serine derivatives). In this case, the levels of stereoselection could be enhanced by using cyclic derivatives derived from Garner's aldehyde.
Identifiersdoi: 10.1002/ejoc.201403488
issn: 1434-193X
e-issn: 1099-0690
Appears in Collections:(IQM) Artículos
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