Abstract
Racemic secondary allylic alcohols were transformed into optically active secondary alcohols by a combined Ru-catalyzed isomerization/asymmetric transfer-hydrogenation reaction. The catalyst was generated in situ in isopropyl alcohol from di-μ-chlorobis[(p-cymene)chlororuthenium(II)], the chiral ligand (1S,2S)-N-(p-tolylsulfonyl)-1,2-diphenylethylenediamine, and K2CO3, and the products were afforded in yields up to 97 % with up to 93 % enantiomeric excess without the use of hydrogen gas. A Hammett study revealed that the reaction rate was enhanced with electron-withdrawing aryl substituents. The reaction supports the recent work published by Adolfsson et al. as new methodology for the synthesis of chiral compounds from allylic alcohols.
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