CHED 489 |
| Enantiomeric pure amines are especially valuable organic compounds that have been used as chiral auxiliaries and catalysts in asymmetric organic transformations and as chiral building blocks for the synthesis of a variety of pharmaceutical compounds. The development of new methods for the asymmetric reduction of O-substituted oximes is very important since it offers a facile and convenient process for the synthesis of primary amines. We discovered that chiral spiroborate esters 3 efficiently catalyze the enantioselective reduction of thiochroman-4-one O-benzyl oximes with only 10 mol % of catalytic load affording the corresponding primary amine 2 in high yield and 99% ee. We are now investigating the reduction of other chroman and thiochroman O-benzyl oximes to study the electronic effects in this reaction. In addition, the synthesis of biological important chiral amines will be presented.
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Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, April 7, 2008 Morial Convention Center -- Hall A, Poster
Division of Chemical Education |
