Carbon-Carbon Bond-Formation via Thioacetals                (Chemistry)
{'Code': '03090003', 'Directorate': {'Abbreviation': 'MPS', 'LongName': 'Direct For Mathematical & Physical Scien'}, 'Division': {'Abbreviation': 'CHE', 'LongName': 'Division Of Chemistry'}}
{'SignBlockName': 'George M. Rubottom'}
Amino acids are the building blocks of proteins, and thus                   they, and their chemistry, occupy an important position in                      biochemistry. Nature is able to efficiently make amino acids in                 a highly specific fashion because it employs enzymes. However,                  many amino acids of potential use are not synthesized by                        nature, and so the chemist is in need of tools to make these                    compounds with the same specificity as found in nature. This                    project in the Organic and Macromolecular Chemistry Program is                  developing such reactions for which the chemistry community                     will have great use.                                                                                                                                                The overall objective of the proposed research is to                        develop efficient and practical methodology for the asymmetric                  synthesis of alpha-amino acids based on carbon-carbon bond                      constructions of electrophilic glycine-derived templates.  In                   addition, the free radical and electrocyclic couplings to these                 glycine-templates will be investigated.  On the practical side,                 access to either D- or L- configured amino acids in high                        optical purity and chemical purity will be the primary utility                  of this research.  These selective coupling reactions will be                   achieved by a careful study of the fundamental chemistry of                     hemi-amino acetals as substrates for cationic and radical                       reactions with a variety of organometallic reagents.                                                                                                            A new organotin acetylide coupling reaction has been discovered                 and will be investigated as a means for preparing vinyl and                     alkynyl alpha-amino acids which have potent biological                          activities.   Several second-generation chiral auxilliaries                     will be investigated to broaden the scope of the electrophilic                  glycine template concept.  The new methodology will be                          demonstrated with total syntheses of several representative,                    complex amino acids.
{'FirstName': 'Robert', 'LastName': 'Williams', 'EmailAddress': 'robert.williams@colostate.edu', 'StartDate': '01/01/1988', 'EndDate': None, 'RoleCode': 'Principal Investigator'}
{'Name': 'Colorado State University', 'CityName': 'Fort Collins', 'ZipCode': '805232002', 'PhoneNumber': '9704916355', 'StreetAddress': '601 S Howes St', 'CountryName': 'United States', 'StateName': 'Colorado', 'StateCode': 'CO'}
{'Code': '1950', 'Text': 'METHODOLOGY'}
{'url': 'https://www.nsf.gov/awardsearch/download?DownloadFileName=1987&All=true', 'xml': '8717017.xml'}