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 interesting reactions have speedily turn into the most present fields in natural chemistry, seeing that they enable attaining simply excessive molecular complexity in an economically beneficial manner with merits of mark downs in solvent, time, strength, and prices. Unsurprisingly, the excessive degrees of potency and enantioselectivity typically 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 lively compounds and average items. The publication is split into 3 primary sections, dealing successively with uneven domino reactions according to using chiral auxiliaries, uneven domino reactions according to using chiral steel catalysts, and uneven domino reactions in keeping with using chiral organocatalysts, protecting the literature because the starting of 2006.
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Extra info for Asymmetric domino reactions
45 Synthesis of pseudolaric acid A through Rh-catalysed domino carbonyl ylide formation–1,3-dipolar cycloaddition reaction. In the same area, Chiu et al. 6 : 1 mixture of two diastereoisomers. The major diastereomer was separated and then converted into pseudolaric acid A through 10 steps. It must be noted that the use of achiral dirhodium catalysts, such as rhodium(II) acetate, favoured the formation of the undesired diastereomer, since in this case the ratio of diastereomers was 1 : 3, combined with a 61% yield.
4]heptane derivative in good yield and relative diastereoselectivity of 498% de. The key step of the process was an SN2-type ring-opening of the TMSOTf-activated azetidine ring by the silyl ketene acetal generated by treatment with TMSOTf and triethylamine (TEA). 32 Domino intramolecular azetidine ring-opening–closing reaction. 32. Remarkably, in this process TMSOTf played a triple role by generating the reactive nucleophilic intermediate (silyl ketene acetal), by activating the azetidine for the nucleophilic ring-opening, and by activating the carbonyl group of the tertiary ester group for the ﬁnal amide bond formation.
39 OTBS N CO2t-Bu Domino intramolecular ynamide benzannulation reaction. 40 Domino oxy-Cope–Claisen–ene reaction. In 2007, Barriault et al. 59 The observed conservation of enantiomeric excess was taken by the authors as evidence that the ring inversion of the intermediary enol ether did not occur before the Claisen reaction. In 2009, Porco et al. 60 This key step of the synthesis involved a Diels–Alder cycloaddition between a diarylcyclopentadienone, which was generated in situ, and a chiral ortho-quinol derived from a retro-Diels–Alder reaction of its dimeric form.
Asymmetric domino reactions by Helene Pellissier, James Spivey