Journal
SYNLETT
Volume 32, Issue 9, Pages 875-884Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0040-1707309
Keywords
P-stereogenic; inversion; chiral phosphine; phosphido; copper
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Funding
- US National Science Foundation [CHE-1562037]
- American Chemical Society Petroleum Research Fund [60035-ND3]
- Dartmouth College
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Metal-catalyzed asymmetric synthesis of P-stereogenic phosphines can produce chiral ligands with valuable applications in asymmetric catalysis, without the need for precious metals. This method can be achieved using earth-abundant metals to develop more active catalysts.
Metal-catalyzed asymmetric synthesis of P-stereogenic phosphines is a potentially useful approach to a class of chiral ligands with valuable applications in asymmetric catalysis. We introduced this idea with chiral platinum and palladium catalysts, exploiting rapid pyramidal inversion in diastereomeric metal-phosphido complexes (ML*(PRR)) to control phosphorus stereochemistry. This Account summarizes our attempts to develop related synthetic methods using earth-abundant metals, especially copper, in which weaker metal-ligand bonds and faster substitution processes were expected to result in more active catalysts. Indeed, precious metals were not required. Without any transition metals at all, we exploited related P-epimerization processes to prepare enantiomerically pure phosphiranes and secondary phosphine oxides (SPOs) from commercially available chiral epoxides.
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