Abstract
Chiral P, N-ferrocene ligands, 1-diphenylphosphino-1′-[( S)-4-isopropyl-2.5-oxazolinyl]-2′-( S p )-(trimethylsilyl)-ferrocene and its diastereomer, and 1-diphenylphosphino-1′-[( S)-4-isopropyl-2.5-oxazolinyl]-2′( S p )-(diphenylphosphino)-ferrocene and its diastereomer were used in the palladium-catalyzed asymmetric hydroesterification of styrene. The role of these ligands, which contain central, axial, and planar chirality, on the stereochemical outcome was investigated. A significant effect of using CuCl 2 as a co-catalyst on the reaction was observed. Excellent regioselectivity (b/n >99:1) with low ee (28%) was obtained in the presence of CuCl 2; moderate enantioselectivity (64% ee) but low regioselectivity (b/n, 40/60) was obtained in the absence of CuCl 2.
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