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18 mM) as the catalyst, a racemic -bromo- -keto phosphonate is hydrogenated at 25  C under 49 50 C–H Bond Formation by Asymmetric and Stereoselective Hydrogenation 4 atm of hydrogen to give the syn-product (1R,2S)- -bromo- -hydroxy phosphonate with 98% ee (Equation (76)). 289,3i Due to lack of secondary coordination to the metal, most chiral Rh or Ru catalysts which are quite effective for functionalized ketones usually cannot provide high enantioselectivity and reactivity for the hydrogenation of unfunctionalized ketones.

Using a BINAPINE–Rh complex as catalyst, a wide C–H Bond Formation by Asymmetric and Stereoselective Hydrogenation range of (Z)-3-aryl-3-(acylamino)acrylic acid derivatives was hydrogenated with both excellent enantioselectivities (96$>99% ee) and reactivity, and turnover numbers up to 10,000 have been achieved. 174 By employing Ru catalyst generated in situ from Ru(COD)(methallyl)2, chiral phosphine ligand (S)-C3-TunePhos, and HBF4, a series of cyclic 3-(acylamino)acrylate was hydrogenated with excellent ee.

The methodology has been used for the synthesis of important chiral intermediates and natural products. 287 ð75Þ An efficient dynamic kinetic resolution is observed when an -bromo- or -acetylamino- -keto phosphate is subjected to the hydrogenation with an Ru–BINAP catalyst under suitable conditions. 18 mM) as the catalyst, a racemic -bromo- -keto phosphonate is hydrogenated at 25  C under 49 50 C–H Bond Formation by Asymmetric and Stereoselective Hydrogenation 4 atm of hydrogen to give the syn-product (1R,2S)- -bromo- -hydroxy phosphonate with 98% ee (Equation (76)).

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Applications II. Transition Metal Compounds in Organic Synthesis 1 by Ojima I.


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