Discovery and development of efficient methods for the enantioseiective 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 of 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 catalysts 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 catalyst 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.

Public Health Relevance

In this program, we develop catalysts that efficiently promote reactions that can be used to prepare, in a timely and cost effective manner, a wide range of molecules that are critical to human health care and would otherwise not be accessible. Therefore, In conjunction with developing new and unique catalysts, we test the utility of such catalysts by applying them to the preparation of biologically active molecules.

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
Special Emphasis Panel (NSS)
Program Officer
Lees, Robert G
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Boston College
Schools of Arts and Sciences
Chestnut Hill
United States
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Meng, Fanke; Haeffner, Fredrik; Hoveyda, Amir H (2014) Diastereo- and enantioselective reactions of bis(pinacolato)diboron, 1,3-enynes, and aldehydes catalyzed by an easily accessible bisphosphine-Cu complex. J Am Chem Soc 136:11304-7
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
Hoveyda, Amir H (2014) Evolution of catalytic stereoselective olefin metathesis: from ancillary transformation to purveyor of stereochemical identity. J Org Chem 79:4763-92
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
Meng, Fanke; McGrath, Kevin P; Hoveyda, Amir H (2014) Multifunctional organoboron compounds for scalable natural product synthesis. Nature 513:367-74
Meng, Fanke; Jung, Byunghyuck; Haeffner, Fredrik et al. (2013) NHC-Cu-catalyzed protoboration of monosubstituted allenes. Ligand-controlled site selectivity, application to synthesis and mechanism. Org Lett 15:1414-7
Kiesewetter, Elizabeth T; O'Brien, Robert V; Yu, Elsie C et al. (2013) Synthesis of Z-(pinacolato)allylboron and Z-(pinacolato)alkenylboron compounds through stereoselective catalytic cross-metathesis. J Am Chem Soc 135:6026-9
Dabrowski, Jennifer A; Gao, Fang; Hoveyda, Amir H (2011) Enantioselective synthesis of alkyne-substituted quaternary carbon stereogenic centers through NHC-Cu-catalyzed allylic substitution reactions with (i-Bu)2(alkynyl)aluminum reagents. J Am Chem Soc 133:4778-81
Lee, Yunmi; Li, Bo; Hoveyda, Amir H (2009) Stereogenic-at-metal Zn- and Al-based N-heterocyclic carbene (NHC) complexes as bifunctional catalysts in Cu-free enantioselective allylic alkylations. J Am Chem Soc 131:11625-33
Lee, Yunmi; Hoveyda, Amir H (2009) Efficient boron-copper additions to aryl-substituted alkenes promoted by NHC-based catalysts. enantioselective Cu-catalyzed hydroboration reactions. J Am Chem Soc 131:3160-1

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