CARB 16 |
| The synthesis of chiral compounds in optically pure form is one of the crucial requirements of modern organic chemistry. We focused our attention on enantioselective methods for the synthesis of 3,6-dihydro-2H-pyran derivatives from activated carbonyl compounds such as alkyl glyoxylates, using hetero-Diels-Alder, Friedel-Crafts and allylation reactions. In our investigations we applied the chiral (salen)Cr(III) and (salen)Co(II) complexes as catalysts. In the case of the Diels-Alder reaction of 1 methoxybuta-1,3-diene with glyoxylates, salen complexes were efficient catalysts. We have also found that the allylation reaction of glyoxylates with allyltributyltin proceeded smoothly for low loading of (salen)CrBF4 under undemanding conditions, to afford homoallylic alcohols. The Friedel-Crafts reaction of 2-substituted furans with glyoxylates in the presence of (salen)Co(II) under high-pressure conditions (10 kbar) was effective as well, to afford furfuryl alcohols with good enantioselectivity. |
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Organic Chemistry of Carbohydrates: Legacy of Aleksander Zamojski
8:30 AM-12:00 PM, Monday, March 26, 2007 McCormick Place North -- Room N226, Level 2, Oral
Division of Carbohydrate Chemistry |