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)
Institute
National Institute of General Medical Sciences (NIGMS)
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
1999-05-01
Project End
2018-07-31
Budget Start
2014-08-01
Budget End
2015-07-31
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
Coombs, John R; Morken, James P (2016) Catalytic Enantioselective Functionalization of Unactivated Terminal Alkenes. Angew Chem Int Ed Engl 55:2636-49
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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
Blaisdell, Thomas P; Morken, James P (2015) Hydroxyl-Directed Cross-Coupling: A Scalable Synthesis of Debromohamigeran E and Other Targets of Interest. J Am Chem Soc 137:8712-5
Gutierrez, Osvaldo; Metil, Dattatray; Dwivedi, Namrata et al. (2015) Practical, asymmetric route to sitagliptin and derivatives: development and origin of diastereoselectivity. Org Lett 17:1742-5
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
Cho, Hee Yeon; Morken, James P (2014) Catalytic bismetallative multicomponent coupling reactions: scope, applications, and mechanisms. Chem Soc Rev 43:4368-80
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
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

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