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Iterative Asymmetric Hydroformylation/Wittig Olefination Sequence


  • We thank The Dow Chemical Company for their donation of [Rh(acac)(CO)2], Dr. Neil Strotman (Merck) for assistance in ligand resolution, and Prof. Tehshik Yoon and co-workers for access to SFC instrumentation. We acknowledge the NSF for funding (CHE-1152989 and a graduate fellowship for GWW). NSF (CHE-9208463 and CHE-9629688) and NIH grants (RR08389-01) funded the NMR facilities at UW-Madison.


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Over and over again: Various alkenes underwent the title reaction in the presence of rhodium/bis(diazaphospholane) complexes to give γ-chiral α,β-unsaturated carbonyl products (46–96 % yield) with high enantioselectivity (90–99 % ee). Iterative sequences of the reaction lead to stereoselective C[BOND]C bond formations between achiral reactants to produce products having multiple stereocenters (see scheme, acac=acetylacetonate).