Organic Chemistry

Download Cycloaddition Reactions in Organic Synthesis by Karola Rück-Braun PDF

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 appropriate details is accrued during this well-structured, functional guide. prepared in keeping with the cycloaddition kind, the correct auxiliaries, reactants, stereoselectivities, yields, and references for every key response are compiled in compact tables. Scientists drawn to the theoretical heritage of stereoselective cycloadditions will locate an outstanding choice of in-depth literature references. ... with this finished info assortment cycloadditions becomes a fair extra strong device for each natural chemist engaged on stereoselective synthesis.

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1]heptadiene derivatives in high optical purity; these derivatives are synthetically useful chiral building blocks. The two 3,5-dimethylbenzyl substituents on the nitrogen atom of the ligand are important determinants of the enantioselectivity. 8 Asymmetric Diels-Alder reactions of alkynyl aldehydes catalyzed by 9 [12] R Yield (%) ee (%) Me3Si Et3Si Me2PhSi Bu3Sn 68 37 50 83 87 85 87 80 as follows: one of the N-CH2Ar substituents serves to block attack on the lower face of the s-trans-coordinated dienophile, whereas the other screens off another region in space and limits the rotation of both the dienophile and the other N-CH2Ar group.

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.

After tuning the ligand of the catalyst, it was discovered that the bis(oxazoline) ligand derived from tert-leucine is effective when Cu(OTf)2 is used as the metal source. Cu(OTf)2 is superior both in chemical and optical yields to the other metal triflates examined – AgOTf, Zn(OTf)2, Cd(OTf)2, Co(OTf)2, Mn(OTf)2, Lu(OT)3, Sm(OTf)3, LiOTf, and Ni(OTf)2 [33a,b]. The effect of the catalyst counter-ions was investigated, revealing its profound influence on both the reaction rate and stereoselectivity.

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