Grantee Research Project Results
Opportunities Offered by Indium-Promoted Carbon-Carbon Bond-Forming Reactions in Water
EPA Grant Number: R824725Title: Opportunities Offered by Indium-Promoted Carbon-Carbon Bond-Forming Reactions in Water
Investigators: Paquette, Leo A.
Institution: The Ohio State University
EPA Project Officer: Aja, Hayley
Project Period: October 1, 1995 through September 30, 1997
Project Amount: $300,000
RFA: Technology for a Sustainable Environment (1995) RFA Text | Recipients Lists
Research Category: Pollution Prevention/Sustainable Development , Sustainable and Healthy Communities
Description:
This research project seeks to generalize on the serviceability of free hydroxyl groups for promoting stereochemical control in organic reactions performed in aqueous environments under catalysis by indium metal. Emphasis is initially being placed on establishing those structural features within carbonyl compounds most conducive to achieving high levels of stereoselectivity. An exemplary thrust involves enforced axial and equatorial orientation of the hydroxyl substituent at alpha- and beta-sites in order to determine their impact on stereoinduction. To be investigated subsequently, will be a wide range of diastereoselective reactions where installation of three or more contiguous stereogenic centers operate. While the initial phases of this investigation shall involve allylic halides for simplicity and convenience, the workability of various other types of potentially reactive halides is also to be probed. It is already clear that tremendous advantages can accrue from the use of the indium-water catalyst system. For example, protection/deprotection steps are no longer necessary. In addition, atom economy is served in an outstanding fashion and reactions proceed at significantly enhanced rates. Should enantioselective addition reactions operate at high levels of chiral induction under these conditions (with added chiral promoter), the project will expand to encompass the full evaluation of these processes as well.Publications and Presentations:
Publications have been submitted on this project: View all 13 publications for this projectJournal Articles:
Journal Articles have been submitted on this project: View all 11 journal articles for this projectSupplemental Keywords:
Green chemistry, carbon-carbon bonding, aqueous and organic solvents, diastereoselection, 1,2 allylindium reagents, thia and a-amino aldehydes in indium-promoted coupling, allelic bromides., Sustainable Industry/Business, RFA, Scientific Discipline, Technology for Sustainable Environment, Chemical Engineering, Sustainable Environment, Environmental Chemistry, Economics and Business, cleaner production/pollution prevention, carbon bond formation, source reduction, waste minimization, aldehydes, pollution prevention, alternative materials, catalysis, indium-promoted carbon bond forming, waste reduction, hydroxyl radicals, cleaner production, allylic halides, environmentally benign solvents, carbon-carbon binding, innovative technology, aqueous solventsProgress and Final Reports:
The perspectives, information and conclusions conveyed in research project abstracts, progress reports, final reports, journal abstracts and journal publications convey the viewpoints of the principal investigator and may not represent the views and policies of ORD and EPA. Conclusions drawn by the principal investigators have not been reviewed by the Agency.