ISSN:
0570-0833
Keywords:
Aldol reaction
;
Synthetic methods
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The present article describes the discovery of a new procedure for aldol condensations for the preparation of α,β-unsaturated carbonyl compoundsG. Wittig, H. Pommer, and W. Stilz, German Patent 1199252 (April 5, 1963), BASF; Chem. Abstr. 63, P 1739c (1965).. The scope of this process is demonstrated by many examples, including some from the natural products sector; at the same time, however, these examples also mark its limitations. The metalated Schiff's bases may be classified as ambident anions; this also explains acylations on the nitrogen. A comparison of the new directed aldol condensation with the formation of unsaturated carbonyl compounds through olefination via phosphorylids shows that the latter method fails when a ketone is used as the substrate. This is where the described procedure using metalated Schiff's bases proves its value.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/anie.196800071
