New functional group transformations can enable synthetic chemists to disconnect molecules in new ways, thereby enabling new synthesis strategies. Ideally such new technologies enable the synthesis of important molecules from untapped, perhaps more readily available, starting materials. In the right context, such methods can prove to be linchpin reactions for total synthesis and can offer new and more efficient routes to useful therapeutic agents. The proposed research will extend our fruitful studies on catalytic diboration reactions into a new range of stereoselective transformations. We will develop new strategies for constructing chiral organoboronates from simple starting materials and use these reactions to solve extant problems in synthesis.

Public Health Relevance

Single-enantiomer chiral compounds are vitally important as new materials and as medicinally relevant therapies. The proposed research will develop new technologies for the construction of such compounds from simple, readily available natural resources.

Agency
National Institute of Health (NIH)
Type
Research Project (R01)
Project #
2R01GM059417-15
Application #
8728520
Study Section
Synthetic and Biological Chemistry B Study Section (SBCB)
Program Officer
Lees, Robert G
Project Start
Project End
Budget Start
Budget End
Support Year
15
Fiscal Year
2014
Total Cost
Indirect Cost
Name
Boston College
Department
Chemistry
Type
Schools of Arts and Sciences
DUNS #
City
Chestnut Hill
State
MA
Country
United States
Zip Code
02467
Cho, Hee Yeon; Morken, James P (2014) Catalytic bismetallative multicomponent coupling reactions: scope, applications, and mechanisms. Chem Soc Rev 43:4368-80
Mlynarski, Scott N; Schuster, Christopher H; Morken, James P (2014) Asymmetric synthesis from terminal alkenes by cascades of diboration and cross-coupling. Nature 505:386-90
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
Hong, Kai; Morken, James P (2013) Catalytic enantioselective one-pot aminoborylation of aldehydes: a strategy for construction of nonracemic *-amino boronates. J Am Chem Soc 135:9252-4
Ferris, Grace E; Hong, Kai; Roundtree, Ian A et al. (2013) A catalytic enantioselective tandem allylation strategy for rapid terpene construction: application to the synthesis of pumilaside aglycon. J Am Chem Soc 135:2501-4
Coombs, John R; Haeffner, Fredrik; Kliman, Laura T et al. (2013) Scope and mechanism of the Pt-catalyzed enantioselective diboration of monosubstituted alkenes. J Am Chem Soc 135:11222-31
Kliman, Laura T; Mlynarski, Scott N; Ferris, Grace E et al. (2012) Catalytic enantioselective 1,2-diboration of 1,3-dienes: versatile reagents for stereoselective allylation. Angew Chem Int Ed Engl 51:521-4
Poe, Sarah L; Morken, James P (2011) A boron-based synthesis of the natural product (+)-trans-dihydrolycoricidine. Angew Chem Int Ed Engl 50:4189-92
Hong, Kai; Morken, James P (2011) Catalytic enantioselective diboration of cyclic dienes. A modified ligand with general utility. J Org Chem 76:9102-8
Schuster, Christopher H; Li, Bo; Morken, James P (2011) Modular monodentate oxaphospholane ligands: utility in highly efficient and enantioselective 1,4-diboration of 1,3-dienes. Angew Chem Int Ed Engl 50:7906-9

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