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Title: | 1,2-stereochemical induction in the Pd<sup>II</sup>-catalyzed conjugate addition of boronic acids |
Authors: | Roscales, S.; Sánchez, Francisco; Csákÿ, Aurelio G. |
Keywords: | Palladium Boron Chiral pool Michael addition Synthetic methods |
Issue Date: | 2015 |
Publisher: | Wiley-VCH |
Citation: | European Journal of Organic Chemistry 2015: 1754-1763 (2015) |
Abstract: | Palladium(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. |
URI: | http://hdl.handle.net/10261/117697 |
DOI: | 10.1002/ejoc.201403488 |
Identifiers: | doi: 10.1002/ejoc.201403488 issn: 1434-193X e-issn: 1099-0690 |
Appears in Collections: | (IQM) Artículos |
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