Catalytic enantioselective Hosomi–Sakurai reaction of α-ketoesters promoted by chiral copper(<scp>ii</scp>) complexes

Niwa, Yutaro; Miyake, Mayu; Hayakawa, Ichiro; Sakakura, Akira

doi:10.1039/c9cc01159e

Cited by 7 publications

(2 citation statements)

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“…When the more reactive methallyltrimethylsilane was employed, both yields and enantioselectivities were significantly improved, presumably due to the increased steric hinderance around the reactive site. The proposed transition state 84 through which the reaction proceeds is shown in Scheme 16 [48] …”

Section: Silyl Olefinsmentioning

confidence: 99%

“…The proposed transition state 84 through which the reaction proceeds is shown in Scheme 16. [48] While much of the work regarding the enantioselective Lewis acid atalysed Hosomi-Sakurai employs the use of a chiral metal species to activate the electrophile, Zhou and co-workers utilized the chiral metal species in an alternative manner. In this mercury atalysed approach, the allyl silane initially reacts with the mercury complex to form allyl mercury species 82, a much more potent nucleophile (Scheme 17).…”

Section: Lewis Acid and Lewis Base Mediated Allylation Of Carbon Elec...mentioning

confidence: 99%

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Strategic Applications of the β‐Silicon Effect

Roberts

McLaughlin

2022

Adv Synth Catal

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Organosilicon reagents are highly versatile and privileged scaffolds in modern synthetic chemistry, largely due to the range of transformations the groups are amenable to. The β‐Silicon effect is one of the fundamental phenomena underpinning the inherent reactivity of organosilicon reagents, allowing unsaturated organosilanes to undergo a range of electrophilic substitutions with a variety of nucleophiles. The application of the β‐Silicon effect in a range of organic transformations is reviewed with the discussion divided up based on the class of silane. The reactivity of these compounds towards carbon, heteroatom and metallic electrophiles is discussed from classical applications such as the Sakurai allylation to contemporary applications such as cross‐coupling chemistry. In addition, examples of these transformations in the context of methodology development and natural product synthesis are provided.

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Section: Silyl Olefinsmentioning

confidence: 99%

Section: Lewis Acid and Lewis Base Mediated Allylation Of Carbon Elec...mentioning

confidence: 99%