In 1999, Jon Owen co-invented a new composition of matter:  3,4-diazaphospholanes.  These compounds are versatile ligands for homogeneous organotransition metal catalysis, especially enantioselective hydroformylation.  Rhodium catalysts ligated to bis(3,4-diazaphospholanes) (BDP) are particularly effective for the regio- and enantioselective synthesis of a-functionalized aldehydes.  Iterative application of Ru-catalyzed Z-selective alkyne hydroacetoxylation, Rh(BDP)-catalyzed enantioselective hydroformylation, and Pinnick aldehyde oxidation enables the atom-efficient, sequence-specific construction of oligoesters.  The absolute configuration of each stereogenic center is independently controlled by the BDP ligand and no coupling agents are required.  Other applications of enantioselective hydroformylation include the catalytic synthesis of unique aldehydes with tertiary and quaternary stereogenic centers and new, iterative hydroformylation/hydroacylation sequences.

Diazaphospholanes and enantioselective catalysis

251st National Meeting (2016)

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