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Asymmetric hydrogen-transfer reduction of prochiral and α,β-unsaturated ketones by iridium complexes containing optically pure aminodiphosphine ligands

✍ Scribed by Claudio Bianchini; Lionel Glendenning; Fabrizio Zanobini; Erica Farnetti; Mauro Graziani; Emese Nagy

Book ID: 104423604
Publisher: Elsevier Science
Year: 1998
Tongue: English
Weight: 185 KB
Volume: 132
Category: Article
ISSN: 1381-1169
DOI: 10.1016/s1381-1169(97)00230-6

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✦ Synopsis

This work reports the catalytic reduction, via hydrogen-transfer from propan-2-ol, of various a ,b-unsaturated ketones or w Ž .Ž .x Ž . unsymmetrical ketones in the presence of Ir COD OMe and the chiral aminodiphosphine ligands R -2 ) Ž . Ž . Ž . Ž . Ž . ) Ž . Ž . PhC H Me N CH CH PR R s Ph, Cy and R -Et C H Me N CH CH PPh . In general, these catalyst systems 2 2 2 2 2 2 2 2

show good activity but modest enantioselectivity. Both the chemoselectivity and the enantioselectivity for the reduction of Ž . a ,b-unsaturated ketones to optically pure allylic alcohols depend on the nature of the substituent s at either the carbon stereocentre or the phosphorus substituents.

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## Abstract A range of __α,β__‐unsaturated acids and esters have been selectively reduced to the corresponding saturated acid derivatives by hydrogen transfer. As the reducing agent, formic acid was used in the presence of Rh^I^ complexes formed with the powerful chiral ligand Ph‐binepine (**1**),