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Chiral α-Branched Mono Phosphine Auxiliaries, Reversal of Sense of Asymmetric Induction Upon Substitution by Peter Kasák; Kurt Mereiter; Michael Widhalm is a Chemistry article available to read on EtoBox.

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A group of 10 (mono-or bis-) a-chiral mono phosphine ligands was synthesized from enantiopure phosphepine sulfide 3 by one or two subsequential highly diastereoselective a-deprotonation/alkylation steps, followed by desulfuration with Raney nickel. Their relative configuration was determined by X-ray crystal structure analysis. The new monophosphine ligands were tested in asymmetric hydrogenation, hydroboration, and Suzuki-Miyaura coupling showing asymmetric inductions up to 91% ee. In the case of hydrogenation, clear evidence was found that enantioselectivity is substantially controlled through a-C chirality rather than through biaryl chirality, which was demonstrated by a change of the sense of asymmetric induction upon change of substituents.

Who reads Chiral α-Branched Mono Phosphine Auxiliaries, Reversal of Sense of Asymmetric Induction Upon Substitution?

Author

Peter Kasák; Kurt Mereiter; Michael Widhalm

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0957-4166)

Published

2005

Language

EN

Field

Chemistry (Physical Sciences)