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The asymmetric hydroformylation of variously N -substituted 4-vinyl β-lactams catalyzed by rhodium aminophosphonite–phosphinite and rhodium aminophosphine–phosphite complexes was studied. These products are valuable intermediates in the preparation of 1-methylcarbapenem antibiotics; the stereoselectivity to the desired β-isomer is related to the presence of a substituent at the N atom of the β-lactam ring. The regioselectivity (branched/linear) but not the stereoselectivity (β/α) was found to be dependent on the substrate to catalyst ratio.

tetrahedron asymmetry

Stereoselective synthesis of 1-methylcarbapenem precursors: studies on the diastereoselective hydroformylation of 4-vinyl β-lactam with aminophosphonite–phosphinite and aminophosphine–phosphite rhodium(I) complexes