By Helene Pellissier, James Spivey
This booklet covers the newest advancements in uneven domino reactions, focussing on these released within the final 6 years. those interesting reactions have quickly develop into essentially the most present fields in natural chemistry, due to the fact they permit achieving simply excessive molecular complexity in an economically beneficial method with benefits of rate reductions in solvent, time, power, and prices. Unsurprisingly, the excessive degrees of potency and enantioselectivity quite often reached in those reactions were exploited for the creation of a large variety of advanced chiral molecules with dense stereochemistry and performance, that are motifs found in biologically energetic compounds and average items. The booklet is split into 3 valuable sections, dealing successively with uneven domino reactions in line with using chiral auxiliaries, uneven domino reactions according to using chiral steel catalysts, and uneven domino reactions in keeping with using chiral organocatalysts, masking the literature because the starting of 2006.
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Extra resources for Asymmetric domino reactions
In 2009, Saba et al. 46 Cu-catalysed domino ammonium ylide formation–[2,3]-rearrangement reaction. 71 The process, mediated by copper, ﬁrst provided a Cu(acac)2-generated metallo carbenoid species, which cyclised to the corresponding spiricyclic ammonium ylide intermediate. This ylide then underwent a [2,3]-rearrangement to aﬀord the ﬁnal chiral tricyclic product as a single stereoisomer in 70% yield. The domino process resulted in a three-carbon expansion of the starting amine ring moiety. Finally, Li et al.
This chiral domino product was further converted into zaragozic acids A and C. 67 Later, Schaus et al. 68 The process evolved through the in situ formation of dipole 31 by treatment of substrate with rhodium(II) acetate dimer in reﬂuxed benzene. 44). 43 Rh-catalysed domino carbonyl ylide formation–1,3-dipolar cycloaddition reaction of a di-tert-butyl D-tartrate-derived diazo ester with 3-butyn-2-one. 44 Rh-catalysed domino carbonyl ylide formation–1,3-dipolar cycloaddition reaction of a chiral dihydropyrimidone diazo ester with a maleimide.
73 Although palladium-catalysed domino processes have only recently been extensively reported in the literature,74 the concept of sequential palladium-mediated transformations was actually pioneered some time before the word ‘‘domino’’ was coined. The discovery of the ability of transition metals to interact with organic moieties, to connect inter- or intramolecularly Asymmetric Domino Reactions Based on the Use of Chiral Substrates 49 alkenes, alkynes, carbon monoxide, etc. in cascading processes, is certainly a breakthrough in organometallic synthesis.
Asymmetric domino reactions by Helene Pellissier, James Spivey