ISSN:
1434-193X
Keywords:
Asymmetric synthesis
;
Density functional calculations
;
Cycloadditions
;
Dihydropyrans
;
Enantioselective oxidations
;
Sulfur heterocycles
;
Sulfoxides
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The 4-benzylidene-3-oxo[1,3]oxathiolan-5-ones 13-15, which were derived from the 3-oxo[1,3]oxathiolan-5-ones 9-11 by Knoevenagel condensation with the aldehydes 12, cyclize in an intramolecular hetero Diels-Alder reaction with high yield and excellent endo/exo as well as induced diastereoselectivity to give the hetero Diels-Alder adducts 16-18. The preferred formation of the Knoevenagel products 13-15 with a (Z) configuration was predicted with DFT calculations (B3LYP-6-311+G*) using the model systems 28 and 29. In addition B3LYP-6-31G*/sB3LYP/3-21G(*) calculations on transition structures for the hetero Diels-Alder reaction of 29 and 30 allowed a good correlation with the experimental results, which show that an endo attack of the dienophile syn to the S-O group in 13-15 leads to the main products.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
