Highly Stereoselective Allylation of Benzaldehyde: Generation of a Stereochemically Defined Allylzinc Species from a π‐Allylpalladium Intermediate and Diethylzinc

Tamaru, Yoshinao; Tanaka, Akihiro; Yasui, Kengo; Goto, Susumu; Tanaka, Shuji

doi:10.1002/anie.199507871

Cited by 92 publications

(24 citation statements)

References 14 publications

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“…In connection with our study, the mechanism of the palladium-catalyzed umpolung allylation [12] and propargylation [13] using Et 2 Zn or Et 3 B might be helpful for understanding the present reaction. The phosphane ligands might no longer be able to exist on the allenyl/propargyl indium reagents provided that the transmetalation is completed.…”

Section: Resultsmentioning

confidence: 85%

Nickel‐Catalyzed Indium(I)‐Mediated syn‐Selective Propargylation of Aldehydes

et al. 2012

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Section: Resultsmentioning

confidence: 85%

Nickel‐Catalyzed Indium(I)‐Mediated syn‐Selective Propargylation of Aldehydes

et al. 2012

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“…The aforementioned palladium-catalyzed allylic substitution (see Section 4.3) formed the basis for a diethylzincmediated umpolung of palladium-allyl complexes. [356][357][358][359][360] Scheme 70. Desymmetrization based on palladium-catalyzed allylic substitution.…”

Section: Allylation and Related Metal-catalyzed Reactionsmentioning

confidence: 99%

Phosphoramidites: Privileged Ligands in Asymmetric Catalysis

Teichert¹,

Feringa²

2010

Angew Chem Int Ed

648

340

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Asymmetric catalysis with transition-metal complexes is the basis for a vast array of stereoselective transformations and has changed the face of modern synthetic chemistry. Key to this success has been the design of chiral ligands to control the regio-, diastereo-, and enantioselectivity. Phosphoramidites have emerged as a highly versatile and readily accessible class of chiral ligands. Their modular structure enables the formation of ligand libraries and easy fine-tuning for a specific catalytic reaction. Phosphoramidites frequently show exceptional levels of stereocontrol, and their monodentate nature is essential in combinatorial catalysis, where a ligand-mixture approach is used. In this Review, recent developments in asymmetric catalysis with phosphoramidites used as ligands are discussed, with a focus on the formation of carbon-carbon and carbon-heteroatom bonds.

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“…Tamaru et al [8] described the formation of allylic zinc derivatives obtained after transmetallation starting from the palladium (p-allyl species. These allylic zinc species react nicely with carbonyl or thiocarbonyl partners to form adducts with high diastereoselectivity.…”

Section: Resultsmentioning

confidence: 99%