Synthetic Applications of the Aza-Achmatowicz Reaction      (Chemistry)
{'Code': '03090003', 'Directorate': {'LongName': 'Direct For Mathematical & Physical Scien'}, 'Division': {'LongName': 'Division Of Chemistry'}}
{'SignBlockName': 'John S. Showell'}
This grant in the Organic and Macromolecular Chemistry Program                  suppports research by Dr. Marco Ciufolini.  The methodology                     being developed by Dr. Ciufolini has the potential for becoming                 a new standard route for the synthesis of nitrogen containing                   materials.  This class of materials is extremely important in                   substances found in both medicine and agriculture.                                                                                                              The rearrangement of N-acyl-2-furylamines to                                    N-acyl-2-alkyl-piperidin-3-ones (termed the "Aza-Achmatowicz"                   reaction) will be developed into a general method for the total                 synthesis of optically active nitrogenous substances.  A key                    step of the new technique involves enzymatic resolution of                      racemic furylglycines.  The resolved aminoacids, which will be                  stereochemically correlated with (L)-Serine, are readily and                    efficiently transformed into valuable building blocks for the                   synthesis of structures as diverse as, e.g., azasaccharides,                    beta-lactams, unusual aminoacids, and amphibian alkaloids.  A                   number of issues in organic methodology will be confronted in                   connection with the total synthesis of members of those general                 classes of compounds.  The stereochemical course of enolate                     alkylations, conjugate additions of organocopper reagents and                   oxidation reactions will be investigated in detail using the                    rearranged materials as substrates.  The directing effect of                    N-centered functionalities on the stereochemical course of                      reactions at neighboring olefinic subunits will be studied.                     New methodology will be developed based on the chemistry of                     enamides.  Ultimately, the Aza-Achmatowicz reaction will be                     refined enough to be used for the construction of N-containing                  carbon frameworks considerably more complex than the ones                       planned in this research.
{'FirstName': 'Marco', 'LastName': 'Ciufolini', 'EmailAddress': 'ciufi@ruf.rice.edu', 'StartDate': '07/01/1987', 'EndDate': None, 'RoleCode': 'Principal Investigator'}
{'Name': 'William Marsh Rice University', 'CityName': 'Houston', 'ZipCode': '770051827', 'PhoneNumber': '7133484820', 'StreetAddress': '6100 MAIN ST', 'CountryName': 'United States', 'StateName': 'Texas', 'StateCode': 'TX'}
{'Code': '1948', 'Text': 'SYNTHESIS'}
{'url': 'https://www.nsf.gov/awardsearch/download?DownloadFileName=1987&All=true', 'xml': '8708130.xml'}