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.
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.
|Liu, Xun; Sun, Chunrui; Mlynarski, Scott et al. (2018) Synthesis and Stereochemical Assignment of Arenolide. Org Lett 20:1898-1901|
|Yan, Lu; Meng, Yan; Haeffner, Fredrik et al. (2018) Carbohydrate/DBU Cocatalyzed Alkene Diboration: Mechanistic Insight Provides Enhanced Catalytic Efficiency and Substrate Scope. J Am Chem Soc 140:3663-3673|
|Liu, Xun; Deaton, T Maxwell; Haeffner, Fredrik et al. (2017) A Boron Alkylidene-Alkene Cycloaddition Reaction: Application to the Synthesis of Aphanamal. Angew Chem Int Ed Engl 56:11485-11489|
|Chierchia, Matteo; Law, Chunyin; Morken, James P (2017) Nickel-Catalyzed Enantioselective Conjunctive Cross-Coupling of 9-BBN Borates. Angew Chem Int Ed Engl 56:11870-11874|
|Fang, Lichao; Yan, Lu; Haeffner, Fredrik et al. (2016) Carbohydrate-Catalyzed Enantioselective Alkene Diboration: Enhanced Reactivity of 1,2-Bonded Diboron Complexes. J Am Chem Soc 138:2508-11|
|Coombs, John R; Morken, James P (2016) Catalytic Enantioselective Functionalization of Unactivated Terminal Alkenes. Angew Chem Int Ed Engl 55:2636-49|
|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|
|Coombs, John R; Zhang, Liang; Morken, James P (2015) Synthesis of vinyl boronates from aldehydes by a practical boron-Wittig reaction. Org Lett 17:1708-11|
|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|
Showing the most recent 10 out of 50 publications