By Karola Rück-Braun
Because the days of Diels, Alder and Woodward, cycloadditions were one of the such a lot flexible reactions for stereoselective synthesis ... All proper info is gathered during this well-structured, functional instruction manual. prepared based on the cycloaddition sort, the best auxiliaries, reactants, stereoselectivities, yields, and references for every key response are compiled in compact tables. Scientists attracted to the theoretical historical past of stereoselective cycloadditions will locate an outstanding collection of in-depth literature references. ... with this finished info assortment cycloadditions becomes an excellent extra robust software for each natural chemist engaged on stereoselective synthesis.
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Fig. 1 Aluminum Corey et al. 14). X-ray structure analysis of the catalyst and 1H and 13C NMR studies revealed that 3-alkenoyl-1,3-oxazolidin-2-one binds with the chiral Lewis acid at a single point, though the dienophile is thought to be a good two-point binding ligand . The dienophile is, moreover, thought to adopt an s-trans conformation in the transition state, while the reaction proceeds through the s-cis conformation for other chiral Lewis acids. This catalyst has also been applied to the Diels-Alder reaction of 5-(benzoxymethyl)-1,3-cyclopentadiene in the synthesis of a key intermediate for prostaglandins.
Although coordination of the three electronegative ligands to a metallic center would be expected to reduce the Lewis acidity, the employment of a non-coordinating counter-ion can, conversely, increase it. 2 The Chiral Lewis Acid-catalyzed Diels-Alder Reaction catalysts, which is a great synthetic advantage. Not only the acryloyl derivative, but also the crotonoyl and cinnamoyl imides react with cyclopentadiene, giving adducts of high optical purity. 51 A transition-state structure was proposed on the basis of the solid-state structure of [Ni((R,R)-DBFOX)(H2O)3](ClO4)2 (Fig.
1 equiv. 1 equiv. 05 equiv. 1 equiv. 1 equiv. 1 equiv. 1 equiv. 1 equiv. 1 equiv. 1 equiv. 2 equiv. 05 equiv. 1 equiv. 1 equiv. 1 equiv. 2 equiv. 2 equiv. 05 equiv. 1 equiv. 05 equiv. 05 equiv. 05 equiv. 05 equiv. 05 equiv. 05 equiv. 05 equiv. –20 8C, 20 h 83%, 2 : 98 97% ee For each reaction the data given are: Amount of catalyst; Temperature, time; Yield, endo/exo; and Optical yield. 05 equiv. 05 equiv. 05 equiv.
Cycloaddition Reactions in Organic Synthesis by Karola Rück-Braun