Chiral Auxiliary Mediated Acyclic Stereocontrol (Chemistry)
{'Code': '03090003', 'Directorate': {'Abbreviation': 'MPS', 'LongName': 'Direct For Mathematical & Physical Scien'}, 'Division': {'Abbreviation': 'CHE', 'LongName': 'Division Of Chemistry'}}
{'SignBlockName': 'John S. Showell', 'PO_EMAI': None, 'PO_PHON': None}
Many important biologically active compounds in nature contain                  atoms other than carbon and oxygen.  Dr.Kurth's                                 research,supported by this grant in the Organic and                             Macromolecular Chemistry Program, will provide new synthetic                    tools for the introduction with stereocontrol of atoms such as                  nitrogen and sulfur.  These should be important in synthesis of                 some of the newer antibiotics.                                                                                                                                  Research will be focused in three separate areas:                                                                                                               I.      Asymmetric ı3,3! sigmatropic rearrangement protocols:                   Catalysis of the aza-Claisen rearrangement will be investigated                 as well as the use of transient `control elements' which enhance                transition-state differentiation in the aza-Claisen, and                        electronic modifications of the aza-heterocycle.  Iterative aza-                Claisen rearrangement and conjugate addition ı3,3! rearrangement                protocols designed to set three contiguous stereocenters will be                investigated as well as chiral auxiliary mediated tandem                        Claisen.Cope rearrangements which will provide high stereocontrol               in C(y) asymmetric induction.                                                                                                                                   II.     Asymmetric olefin cyclization reactions:  The lactonization             of 1,6-heptadiene-4 carboxylic acids will be investigated as well               as the hydrolysis products of iterative aza-Claisen                             rearrangements.  The resulting substrates will possess 4                        contiguous stereogenic centers.  The stereo- and regioselective                 lactamization reactions of oxazolines will be investigated.  The                resulting lactams will possess from 2 to 4 stereogenic centers.                 The stereo- and regioselective olefin amination reactions of                    oxazolins will be investigated.                                                                                                                                 III.    Asymmetric ı2,3! sigmatropic rearrangement protocols:                   The preparation and S-allylation reactions of thioxanones will be               studied as well as both inter- and intramolecular allylation                    protocols.  A detailed study of the ı2,3! sigmatropic                           rearrangements of allylic sulfur ylids will be undertaken and a                 variety of functional group manipulations designed to exploit the               latent functionality and stereochemistry of these ı2,3!                         rearrangement products will be explored.
{'FirstName': 'Mark', 'LastName': 'Kurth', 'PI_MID_INIT': 'J', 'PI_SUFX_NAME': None, 'PI_FULL_NAME': 'Mark J Kurth', 'EmailAddress': 'kurth@chem.ucdavis.edu', 'NSF_ID': '000390890', 'StartDate': '09/01/1987', 'EndDate': None, 'RoleCode': 'Principal Investigator'}
{'Name': 'University of California-Davis', 'CityName': 'DAVIS', 'ZipCode': '956186153', 'PhoneNumber': '5307547700', 'StreetAddress': '1850 RESEARCH PARK DR STE 300', 'StreetAddress2': None, 'CountryName': 'United States', 'StateName': 'California', 'StateCode': 'CA', 'CONGRESSDISTRICT': '04', 'CONGRESS_DISTRICT_ORG': 'CA04', 'ORG_UEI_NUM': 'TX2DAGQPENZ5', 'ORG_LGL_BUS_NAME': 'UNIVERSITY OF CALIFORNIA, DAVIS', 'ORG_PRNT_UEI_NUM': 'NUDGYLBB4S99'}
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{'Code': '1948', 'Text': 'SYNTHESIS'}
{'url': 'https://www.nsf.gov/awardsearch/download?DownloadFileName=1987&All=true', 'xml': '8704836.xml'}