. New strategies for constructing chiral organic molecules can have a significant impact on the production of important medicinally-active compounds and organic materials. The proposed research will develop an unprecedented catalytic conjunctive coupling reaction that results in the combination of three readily available simple organic molecules and establishes a product with a two new C- C bonds and a boron-containing stereogenic center. The reactivity manifold described is the first of its kind and it promises to result in the introduction of an array of new reactions to accomplish the stereoselective synthesis of important chiral compounds.

Public Health Relevance

. Enantiomerically-enriched chiral compounds are important materials in the pharmaceutical industry and have applications in the study of biological processes. The proposed research aims to introduce new processes for the inexpensive, efficient, and selective production of such chiral compounds under the influence of small amounts of specially designed catalysts. In this regards, it can be anticipated that the proposed research will have a significant impact on human healthcare.

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
5R01GM118641-02
Application #
9404464
Study Section
Synthetic and Biological Chemistry A Study Section (SBCA)
Program Officer
Lees, Robert G
Project Start
2017-01-01
Project End
2018-12-31
Budget Start
2018-01-01
Budget End
2018-12-31
Support Year
2
Fiscal Year
2018
Total Cost
Indirect Cost
Name
Boston College
Department
Chemistry
Type
Schools of Arts and Sciences
DUNS #
045896339
City
Chestnut Hill
State
MA
Country
United States
Zip Code
Edelstein, Emma K; Namirembe, Sheila; Morken, James P (2017) Enantioselective Conjunctive Cross-Coupling of Bis(alkenyl)borates: A General Synthesis of Chiral Allylboron Reagents. J Am Chem Soc :
Lovinger, Gabriel J; Aparece, Mark D; Morken, James P (2017) Pd-Catalyzed Conjunctive Cross-Coupling between Grignard-Derived Boron ""Ate"" Complexes and C(sp2) Halides or Triflates: NaOTf as a Grignard Activator and Halide Scavenger. J Am Chem Soc 139:3153-3160
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