Dichloro{(R)-(+)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl}[(2R)-(-)-1,1-bis(4-methoxyphenyl)-3-methyl-1,2-butanediamine]ruthenium(II)

Reaction

1. Highly active catalyst for hydrogenation of simple ketones giving high enantioselectivity when sterically unsymmetrical ketones such as acetophenone, heteroaryl ketones, benzophenones, cyclopropyl ketones, and cyclohexyl ketones are substrates. Ee's are enhanced with XylBINAP relative to BINAP. The otherwise poorly bonded ketone is held in the transition state by hydrogen bonding to the protic bidentate amine.
2. Carbonyl groups are selectively reduced even when olefins exist in the same molecule.
3. In the presence of strong base, and catalyst, simple ketones, having substituents at the α-position, may be induced to undergo dynamic kinectic resolution during their hydrogenation to produce two chiral carbon centers in high yield.

Uses

Chiral RuCl2(diphosphine)?(1,?2-?diamine) complexes catalyzes the asymetrical hydrogenation of amino ketones. E.g., hydrogenation of MeCOCH2NMe2 in presence of trans-?RuCl2[(R)?-?xylbinap]?[(R)?-?daipen] gave 79?% (S)?-?MeCH(OH)?CH2NMe2. This compound was used as a catalyst.