Abstract
The asymmetric hydroformylation of N-acylaminoacrylic acid esters 1 is efficiently catalysed by HRh(CO)(PPh 3) 3 in the presence of DIOP and related diphosphines as chiral ligands. The reaction is completely regioselective and affords in high yield the more branched aldehyde with the formyl group linked to a quaternary stereocenter. Irrespective of the structure of 1, preferential insertion of carbon monoxide always occurs onto the Re face of the substrate giving the (R)-antipodes in up to 60% enantioselectivity. Due to self enrichment during crystallisation, aldehyde 2b is readily isolated in 70–75% e.e.
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