A hydrogen borrowing reaction employing secondary alcohols and Ph* (Me5C6) ketones to give beta-branched carbonyl products is described (21 examples). This new C-C bond forming process requires low loadings of [Cp*IrCl2](2), relatively low temperatures, and up to 2.0 equiv of the secondary alcohol. Substrate induced diastereoselectivity was observed, and this represents the first example of a diastereoselective enolate. hydrogen borrowing alkylation. By utilizing the Ph* group, the beta-branched products could be straightforwardly cleaved to the corresponding esters or amides using a retro-Friedel Crafts reaction. Finally, this protocol was applied to the synthesis of fragrance compound (+/-)-3-methy1-5-phenylpentanol.