Synthesis of Monodentate Chiral Spiro Phosphonites and the Electronic Effect of Ligand in Asymmetric Hydrogenation
- 21 October 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (23) , 8157-8160
- https://doi.org/10.1021/jo049146x
Abstract
New monodentate chiral phosphonites were synthesized from enantiomerically pure 1,1‘-spirobiindane-7,7‘-diol. The phosphonites 2 were efficient ligands for the Rh-catalyzed asymmetric hydrogenation of α- and β-dehydroamino acid derivatives, providing the amino acids in high enantioselectivities. The study of electronic effect showed that the electron-withdrawing substitutent on the P-phenyl ring of the phosphonite ligand dramatically decreased both the reactivity and enantioselectivity of the ligand.Keywords
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