Abstract

The proposed research will continue our efforts in the development of alkene diboration reactions. These transformations allow the selective conversion of inexpensive alkene and diene substrates into single enantiomer chiral compounds. Notably, the types of reaction products that arise from these new processes are difficult to make with other technologies. In the proposed work, we will study the mechanism of enantioselective diboration reactions so that we can develop more efficient catalysts. We will also introduce new chiral monodentate ligand structures that should be useful for the diboration reaction and other processes as well. Lastly, we will explore the utility of these processes to solve extant problems in asymmetric synthesis.

Public Health Relevance

Single enantiomer chiral compounds are important structures in modern human therapeutics. The handedness: that accompanies types of structures enables them to :fit: into physiological drug targets. The proposed research aims to develop new processes that allow for the economical construction of these types of chemical compounds.

  Funding Agency

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
5R01GM059417-14
Application #
8461684
Study Section
Synthetic and Biological Chemistry A Study Section (SBCA)
Program Officer
Lees, Robert G
Project Start
1999-05-01
Project End
2014-04-30
Budget Start
2013-05-01
Budget End
2014-04-30
Support Year
14
Fiscal Year
2013
Total Cost
$282,578
Indirect Cost
$102,017

  Institution

Name
Boston College
Department
Chemistry
Type
Schools of Arts and Sciences
DUNS #
045896339
City
Chestnut Hill
State
MA
Country
United States
Zip Code
02467

  Publications

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

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