New methods for catalytic enantioselective construction of C-C bonds are fundamentally significant. In the right context, such methods can prove to be lynchpin reactions for total synthesis and they can offer new and more efficient routes to useful therapeutic agents. Along these lines, single enantiomer chiral compounds are vitally important as new materials and as medicinally relevant therapies. Indeed, one recent review article established that as of 2003, fully 50% of new drugs brought to market are single enantiomer chiral entities. Further, it was estimated that 500-1000 single enantiomer compounds are in the global drug pipeline at any one time. Clearly, our ability to prepare such chiral therapeutic agents can be enhanced substantially by the introduction of catalytic enantioselective chemical transformations that result in fundamentally new synthetic disconnections. The proposed research will extend our fruitful studies on catalytic conjugate allylation reactions to a much broader range of enantioselective cross-coupling reactions.

Public Health Relevance

Enantiomerically-enriched chiral compounds are important structures in modern health care. The chirality that accompanies these types of compounds may enable them to fit into physiological drug targets better than flat structures thereby offering more potent therapeutics. The proposed research aims to develop new reactions that will provide more accessible routes to such chiral molecular entities.

National Institute of Health (NIH)
National Institute of General Medical Sciences (NIGMS)
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Special Emphasis Panel (ZRG1-BCMB-B (02))
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Lees, Robert G
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Boston College
Schools of Arts and Sciences
Chestnut Hill
United States
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Potter, Bowman; Edelstein, Emma K; Morken, James P (2016) Modular, Catalytic Enantioselective Construction of Quaternary Carbon Stereocenters by Sequential Cross-Coupling Reactions. Org Lett 18:3286-9
Zhang, Liang; Lovinger, Gabriel J; Edelstein, Emma K et al. (2016) Catalytic conjunctive cross-coupling enabled by metal-induced metallate rearrangement. Science 351:70-4
Eno, Meredith S; Lu, Alexander; Morken, James P (2016) Nickel-Catalyzed Asymmetric Kumada Cross-Coupling of Symmetric Cyclic Sulfates. J Am Chem Soc 138:7824-7
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Ely, Robert J; Yu, Zhiyong; Morken, James P (2015) Diastereoselective Ni-catalyzed 1,4-hydroboration of chiral dienols. Tetrahedron Lett 56:3402-3405
Yu, Zhiyong; Eno, Meredith S; Annis, Alexandra H et al. (2015) Enantioselective Hydroformylation of 1-Alkenes with Commercial Ph-BPE Ligand. Org Lett 17:3264-7
Ardolino, Michael J; Morken, James P (2014) Congested C-C bonds by Pd-catalyzed enantioselective allyl-allyl cross-coupling, a mechanism-guided solution. J Am Chem Soc 136:7092-100
Le, Hai; Batten, Amanda; Morken, James P (2014) Catalytic stereospecific allyl-allyl cross-coupling of internal allyl electrophiles with AllylB(pin). Org Lett 16:2096-9
Schuster, Christopher H; Coombs, John R; Kasun, Zachary A et al. (2014) Enantioselective carbocycle formation through intramolecular Pd-catalyzed allyl-aryl cross-coupling. Org Lett 16:4420-3
Yu, Zhiyong; Ely, Robert J; Morken, James P (2014) Synthesis of (+)-discodermolide by catalytic stereoselective borylation reactions. Angew Chem Int Ed Engl 53:9632-6

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