Chemical Engineering

Asymmetric domino reactions by Helene Pellissier, James Spivey

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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 attention-grabbing reactions have swiftly turn into probably the most present fields in natural chemistry, on the grounds that they permit achieving simply excessive molecular complexity in an economically beneficial method with merits of reductions in solvent, time, power, and prices. Unsurprisingly, the excessive degrees of potency and enantioselectivity mostly 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 according to using chiral auxiliaries, uneven domino reactions according to using chiral steel catalysts, and uneven domino reactions in line with using chiral organocatalysts, protecting the literature because the starting of 2006.

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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. 61 In this work, the authors have accomplished a parallel screen of cycloaddition partners for ortho-quinols using a plate-based microwave system.

47, the palladium-catalysed domino carbopalladation–Heck reaction of chiral alkynes provided the corresponding tetrasubstituted helical alkenes as single diastereomers in high yields. While enantiopure syn-diastereomers provided good results, the reaction of antidiastereomers did not achieve the corresponding domino helical alkenes. 47. In 2009, Roy et al. 48). This intermediary Heck product could be further converted, by treatment with NaOMe in methanol, into the corresponding domino product in 83% yield.

It must be remembered that the astonishing simplicity of achieving many complex polycyclisations is sometimes directly proportional to the labour required for the synthesis of the cyclisation precursor. The possible modes by which an organopalladium complex can be engaged in consecutive bond formations, or the manner in which two sequential palladium-catalysed processes can be coupled using a single catalytic system, is only limited by the chemist’s imagination. 77 As a recent example, Tietze et al.

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