Asymmetric Oxidations Using Optically Active 2-Sulfonyl-    oxaziridines (Chemistry)
{'Code': '03090003', 'Directorate': {'Abbreviation': 'MPS', 'LongName': 'Direct For Mathematical & Physical Scien'}, 'Division': {'Abbreviation': 'CHE', 'LongName': 'Division Of Chemistry'}}
{'SignBlockName': 'George M. Rubottom', 'PO_EMAI': None, 'PO_PHON': None}
The Organic and Macromolecular Chemistry Program is                        supporting this research which is aimed at studying the ability                 of novel three-membered ring compounds to introduce oxygen                      atoms into a variety of organic substrates in a highly specific                 fashion.  These reagents are characterized by being relatively                  stable, easily handled, crystalline compounds which can be used                 to oxidize both acid- and base-sensitive compounds.                                                                                                                  The major objective of the ongoing research is to                          understand the origins of asymmetric induction (molecular                       recognition), in particular those forces that control the                       asymmetric oxidation of nonfunctionalized substrates (alkenes,                  sulfides and selenides).  The ultimate goal of these                            investigations is the development of reagents and methodologies                 for the reagent-controlled asymmetric oxidation of prochiral                    substrates in high optical purity and with predictable                          stereochemistry.  These goals are being met through the use of                  chiral nonracemic 2-sulfonyloxaziridines.  These reagents,                      which have different active site structures, are uniquely                       qualified for studies of the origins of molecular recognition                   because they i) have well defined active sites, ii) are easily                  modified and iii) are stable.                                                                                                                                        A second goal of this work is the development of catalytic                 oxidizing systems based on the high selectivity of                              2-sulfonyloxaziridines.  The prime objective here is to devise                  an optically active catalytic system, which mimics the                          efficiencies and stereoselectivities of enzymatic                               oxidations,i.e., artificial-enzyme catalysts.                                                                                                                        2-Sulfonyloxaziridines are aprotic and neutral oxidizing                   reagents.  This feature makes possible studies of unusually                     acid-sensitive molecules and studies of the hydroxylation of                    carbanions.  In this regard, the chemistry of the alpha-alkoxy                  and alpha-amino epoxides is being explored.  The oxidation of                   organometallic reagents (RM, vinyllithium compounds) as new                     routes to alcohols, phenols, lactones, enolate stereoisomers                    and optically active alpha-hydroxy carbonyl compounds is being                  pursued.
{'FirstName': 'Franklin', 'LastName': 'Davis', 'PI_MID_INIT': 'A', 'PI_SUFX_NAME': None, 'PI_FULL_NAME': 'Franklin A Davis', 'EmailAddress': 'fdavis@temple.edu', 'NSF_ID': '000167653', 'StartDate': '06/01/1988', 'EndDate': None, 'RoleCode': 'Principal Investigator'}
{'Name': 'Drexel University', 'CityName': 'PHILADELPHIA', 'ZipCode': '191042875', 'PhoneNumber': '2158956342', 'StreetAddress': '3141 CHESTNUT ST', 'StreetAddress2': None, 'CountryName': 'United States', 'StateName': 'Pennsylvania', 'StateCode': 'PA', 'CONGRESSDISTRICT': '03', 'CONGRESS_DISTRICT_ORG': 'PA03', 'ORG_UEI_NUM': 'XF3XM9642N96', 'ORG_LGL_BUS_NAME': 'DREXEL UNIVERSITY', 'ORG_PRNT_UEI_NUM': None}
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{'url': 'https://www.nsf.gov/awardsearch/download?DownloadFileName=1988&All=true', 'xml': '8800471.xml'}