By Helene Pellissier, James Spivey
This e-book covers the most recent advancements in uneven domino reactions, focussing on these released within the final 6 years. those attention-grabbing reactions have speedily develop into probably the most present fields in natural chemistry, in view that they permit achieving simply excessive molecular complexity in an economically beneficial manner with benefits of discounts in solvent, time, power, and prices. Unsurprisingly, the excessive degrees of potency and enantioselectivity regularly reached in those reactions were exploited for the construction of a large variety of complicated chiral molecules with dense stereochemistry and performance, that are motifs found in biologically energetic compounds and common items. The e-book is split into 3 imperative sections, dealing successively with uneven domino reactions in response to using chiral auxiliaries, uneven domino reactions according to using chiral steel catalysts, and uneven domino reactions in accordance with using chiral organocatalysts, protecting the literature because the starting of 2006.
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35). Indeed, the ﬁrst coordination– activation between the Lewis acid and the epoxide moiety of the epoxide led to an epoxide ring-opening and the formation of intermediate 25, which further produced intermediate 26 through the migration of the C5 methyl group to the C4 carbocation centre. Intermediate 26 underwent a 1,2-hydride shift from the C10 position to the C5 carbocation centre on the a-face of the molecule to provide intermediate 27, wherein the C10 carbocation centre was trapped by the inner phenolic hydroxyl group to deliver, after elimination of the Lewis acid, the ﬁnal desired cyclised product.
In 2008, Fustero et al. 25 Domino elimination–1,6-addition reaction. 26 Synthesis of (þ)-chinensiolide B through domino allylboration– lactonisation reaction. 27 Domino nucleophilic addition–nucleophilic aromatic substitution reaction. including a nucleophilic addition of the carbanion of chiral 2-p-tolylsulﬁnyl alkylbenzenes, generated in the presence of lithium diisopropylamide (LDA) as a base, to ﬂuorinated aldimines and ketimines. 42 In the same year, Garrido et al. 28, the reaction of Baylis–Hillman adducts with a chiral lithium amide aﬀorded the corresponding chiral g-substituted d-amino acids in moderate to good yields, combined with both high diastereo- and enantioselectivities of up to 495% de and ee, respectively.
In these processes, a carbocation is formed, either formally or in reality. This carbocation can be formed by elimination, or by addition of a positive particle such as a proton. The carbocation then reacts with a nucleophile to form a new carbocation that undergoes one or more comparable further transformations in a cationic–cationic process, ﬁnally being trapped by a nucleophile or stabilised by elimination of a proton. As an example, a diastereoselective cationic domino cyclisation was employed by Blaauw et al.
Asymmetric domino reactions by Helene Pellissier, James Spivey