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Akhtar, Wasim M; Cheong, Choon Boon; Frost, James R; Christensen, Kirsten E; Stevenson, Neil G; Donohoe, Timothy J
Journal of the American Chemical Society, 02/2017, Volume: 139, Issue: 7Journal Article
A hydrogen borrowing reaction employing secondary alcohols and Ph* (Me5C6) ketones to give β-branched carbonyl products is described (21 examples). This new C–C bond forming process requires low loadings of Cp*IrCl22, 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 β-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-methyl-5-phenylpentanol.
