Discovery and development of efficient methods for the enantioselective synthesis (preparation of a handed molecule in a single hand form) of organic molecules is critical to the successful development of efficacious new therapeutics. Such methods allow therapeutics to become accessible in a highly desirable pure form, at a low cost and without generation of toxic side products. Such factors that can significantly reduce the amount time between the initial discovery and availability to patients from all economic segments of the society. Among such useful synthesis methods, those that are promoted by a catalyst (where small amounts of a catalyst lead to a lot of highly valuable product) and promote carbon-carbon bond formation (one of the most common bonds in nature) are particularly significant. In this proposal, we propose to design, discover and develop several new and user-friendly catalysts for the preparation of C-C bonds that will prove critical to the synthesis of a wide range of medicinally important and biologically active molecules. Our projects will have several important features: a) They focus on new catalysts that can be used on other important reactions and not just those that will be studied by us; that is, our new catalysts will have a broad impact on the research of scientists elsewhere interested in accomplishing the above goals, b) Our studies focus on the development of methods that deliver important molecules that cannot be prepared by any other protocol, or if they can, they are far less efficient. We will design and develop methods that allow chemists to take readily available and relatively inexpensive materials and convert them, with the aid of catalysts developed in this project, to highly valuable compounds that can be used to access precious medicinally active agents. In addition to designing new catalysts and methods, through applications to synthesis of biologically active molecules, we are also interested in demonstrating the utility of such methods, as well as identifying their shortcomings.

National Institute of Health (NIH)
National Institute of General Medical Sciences (NIGMS)
Method to Extend Research in Time (MERIT) Award (R37)
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Study Section
Medicinal Chemistry Study Section (MCHA)
Program Officer
Schwab, John M
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Boston College
Schools of Arts and Sciences
Chestnut Hill
United States
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Huang, Youming; Del Pozo, Juan; Torker, Sebastian et al. (2018) Enantioselective Synthesis of Trisubstituted Allenyl-B(pin) Compounds by Phosphine-Cu-Catalyzed 1,3-Enyne Hydroboration. Insights Regarding Stereochemical Integrity of Cu-Allenyl Intermediates. J Am Chem Soc 140:2643-2655
Lee, Jaehee; Radomkit, Suttipol; Torker, Sebastian et al. (2018) Mechanism-based enhancement of scope and enantioselectivity for reactions involving a copper-substituted stereogenic carbon centre. Nat Chem 10:99-108
Lee, Jaehee; Torker, Sebastian; Hoveyda, Amir H (2017) Versatile Homoallylic Boronates by Chemo-, SN 2'-, Diastereo- and Enantioselective Catalytic Sequence of Cu-H Addition to Vinyl-B(pin)/Allylic Substitution. Angew Chem Int Ed Engl 56:821-826
Li, Xiben; Meng, Fanke; Torker, Sebastian et al. (2016) Catalytic Enantioselective Conjugate Additions of (pin)B-Substituted Allylcopper Compounds Generated in situ from Butadiene or Isoprene. Angew Chem Int Ed Engl 55:9997-10002
Shi, Ying; Hoveyda, Amir H (2016) Catalytic SN2'- and Enantioselective Allylic Substitution with a Diborylmethane Reagent and Application in Synthesis. Angew Chem Int Ed Engl 55:3455-8
Meng, Fanke; Li, Xiben; Torker, Sebastian et al. (2016) Catalytic enantioselective 1,6-conjugate additions of propargyl and allyl groups. Nature 537:387-393
Shi, Ying; Jung, Byunghyuck; Torker, Sebastian et al. (2015) N-Heterocyclic Carbene-Copper-Catalyzed Group-, Site-, and Enantioselective Allylic Substitution with a Readily Accessible Propargyl(pinacolato)boron Reagent: Utility in Stereoselective Synthesis and Mechanistic Attributes. J Am Chem Soc 137:8948-64
McGrath, Kevin P; Hoveyda, Amir H (2014) A multicomponent Ni-, Zr-, and Cu-catalyzed strategy for enantioselective synthesis of alkenyl-substituted quaternary carbons. Angew Chem Int Ed Engl 53:1910-4
Jang, Hwanjong; Jung, Byunghyuck; Hoveyda, Amir H (2014) Catalytic enantioselective protoboration of disubstituted allenes. Access to alkenylboron compounds in high enantiomeric purity. Org Lett 16:4658-61
Gao, Fang; Carr, James L; Hoveyda, Amir H (2014) A broadly applicable NHC-Cu-catalyzed approach for efficient, site-, and enantioselective coupling of readily accessible (pinacolato)alkenylboron compounds to allylic phosphates and applications to natural product synthesis. J Am Chem Soc 136:2149-61

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