Simple exploration of (R)-4-Benzyl-2-oxazolidinone

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Stereoselective catalytic hydrogenation and conjugate reduction of 4-methyl itaconate derivatives bearing a chiral auxiliary

The catalytic hydrogenation of 4-methyl itaconate derivatives bearing a chiral auxiliary and their conjugate reduction with n-Bu3SnH in the presence of Lewis acid were examined to reveal their diastereoselectivity. The homogeneous catalytic hydrogenation of 4-methyl itaconyl (1S)-(-)-2,10- camphorsultam with the Crabtree’s catalyst [Ir(COD)(PCy3)(py)]PF 6 in CH2Cl2-MeOH (2:1 v/v) gave less polar (1S,2?S)-diastereomer in 84% yield, while the conjugate reduction of the alpha-methylene amide with n-Bu3SnH (2 equiv) using MgI2 (7 equiv) as an additive in CH2Cl2 gave more polar (1S,2?R)-diastereomer in 70% yield.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H1899NO – PubChem