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| - Proline-Based P, N Ligands in Asymmetric Allylation and theHeck Reaction
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| - A series of phosphine−oxazoline ligands based on proline are reported. These ligands are synthesizedfrom commercially available trans-4-hydroxy-l-proline in four steps. The ability of this type of ligandto catalyze allylic alkylation in an asymmetric fashion as well as the asymmetric Heck reaction isreported. The best of these ligands gave a palladium complex, which catalyzed the addition ofdimethylmalonate to cyclopentenyl acetate in excellent yield and up to 96% ee. This same systemcatalyzed the Heck reaction between dihydrofuran and cyclohexene in up to 86% ee. These ligandsappear to differ from the traditional phosphine−oxazoline ligands in that the stereochemistry ofthe stereogenic carbon next to the oxazoline is not necessarily the dominant chiral center in theinduction of selectivity.
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