Stereoselective Heterocyclic Synthesis I by Lutz F. Tietze, Georg Kettschau (auth.), Prof. Dr. Peter

By Lutz F. Tietze, Georg Kettschau (auth.), Prof. Dr. Peter Metz (eds.)

This two-volume set offers fascinating new advancements in preparative heterocyclic chemistry with a unique emphasis at the stereoselective synthesis of - or due to - heterocycles.
A wide variety of contemporary tools and methods for the development and artificial elaboration of flexible heterocycles is surveyed intensive by way of top researchers during this field.
Due to the prime quality and updated insurance of every bankruptcy, this two-volume set presents a important evaluate of the several points mentioned and should even as be hugely inspiring for the professional man made natural chemist in addition to the non-specialist reader.

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Wyler et al. [146a-c] have focused on the hetero Diels-Alder reaction of ct,flunsaturated-acyl cyanides such as 2-140 with ethyl vinyl ether, N-methylated uracil and 1-bromo-2-ethoxyethenes 2-141. In the latter case the dihydropyran L. E Tietze 9G. 6"1 Fig. 4 6"1 75 61 46 Fig. ,,t~ 2-139 2-138 a'R=Ph b" R = CH 3 ""IR5 Fig. 2-37 35 Hetero Diels-Alder Reactions in Organic Chemistry 2-142 was obtained, which could be transformed into stable pyrans by elimination of hydrogen bromide. The yields were good, however, the selectivity, except for the reaction of 2o140c and 2-141 a, was rather low (Fig.

H --. *eo#~,~ C O , M e CO2Me CO2Me 3-52 (38 %) Fig. 3-16 3-53 (29 %) whole domino process [275]. The described methodology basing on cationic 2-aza-l,3obutadienes takes advantage of the enhanced reactivity of iminium ions and has successfully been applied to the stereoselective preparation of 1,2,3,4-tetrahydroquinolines [276, 277]. Activation of 2-azaol,3-butadienes for inverse electron demand aza DielsAlder reactions can also be achieved by introducing electron-withdrawing substituents. Thus, Barluenga's group has developed 3,4-bismethoxycarbonyl-2azao 1,3obutadienes which undergo smooth intramolecular cycloadditions upon heating [278].

2-122a could easily be desulfurized to give either the tetrahydropyran 2-124 or the dihydropyran 2-125. Of importance was the finding that the reaction with the thioenol ether 2-121b shows an excellent endo-selectivity (22:1) (Fig. 2-33). Interestingly, oxabutadienes with an S-alkyl group at C-3 such as 2-126, 2-127 and 2-128 do not react, whereas 2-129 with an S-phenyl group again undergoes a cycloaddition. This clearly shows that activation of the oxabutadiene is caused by a kind of conjugation with the phenyl group over the sulfur atom [142].

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