Asymmetric hydrogenation approaches to valuable, acyclic 1,3-hydroxymethyl chirons.
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An iridium carbene oxazoline complex was used to catalyze hydrogenations of trisubstituted alkenes to give terminal and internal 1,3-hydroxymethyl chirons. The products are accessible in all possible stereoisomeric forms. These hydrogenations do not require strongly coordinating functionalities on the substrate, and in some key cases, catalyst- rather than substrate-controlled stereoselectivities are observed. It is hypothesized that these reactions would not be feasible using iridium or rhodium diphosphine complexes.
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