Palladium-catalyzed asymmetric tandem allylic substitution using chiral 2-(phosphinophenyl)pyridine ligand

K, Ito; Imahayashi, Yoshikatsu; Kuroda, Tomomi; Eno, Shuuichiro; Saito, Bunnai; Katsuki, Tsutomu

doi:10.1016/j.tetlet.2004.08.014

Cited by 49 publications

(11 citation statements)

References 18 publications

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“…[178] This protocol has been applied to the total synthesis of NAS-181. [178] However, the reaction of 2-butene-1,4-biscarbonate in the presence of pyridine-phosphane ligand L67, [180] chiral BHMP-b-Ala L169, [181] (S)-MeO-biphep L170, [182] or (R)-binap ((R)-L117) [183] afforded the related products with low to modest enantioselectivity (44-71.4 % ee).…”

Section: Formation Of Linear Productsmentioning

confidence: 99%

Metal‐Catalyzed Enantioselective Allylation in Asymmetric Synthesis

2007

Angew Chem Int Ed

1,394

431

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Metal-catalyzed enantioselective allylation, which involves the substitution of allylic metal intermediates with a diverse range of different nucleophiles or S(N)2'-type allylic substitution, leads to the formation of C-H, -C, -O, -N, -S, and other bonds with very high levels of asymmetric induction. The reaction may tolerate a broad range of functional groups and has been applied successfully to the synthesis of many natural products and new chiral compounds.

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Section: Formation Of Linear Productsmentioning

confidence: 99%

Metal‐Catalyzed Enantioselective Allylation in Asymmetric Synthesis

2007

Angew Chem Int Ed

1,394

431

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“…201 All the reactions were carried out using [Pd(C 3 H 5 )Cl] as catalyst in CH 2 Cl 2 at room temperature employing various nucleophiles.…”

Section: Heterocyclization Reactions With Alkenesmentioning

confidence: 99%

Recent Development in Palladium-Mediated Synthesis of Oxygen Heterocycles

Majumdar¹,

Chattopadhyay²,

Maji³

et al. 2010

HETEROCYCLES

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“…On the other hand, palladium-catalyzed asymmetric tandem allylic substitution of ( Z )-1,4-bis(isopropoxycarbonyloxy)-2-butene ( 24 ) with the nucleophile 1,2-bis-(benzylamino)ethane ( 16 ), employing 2-(phosphinophenyl)pyridine ( 25 ) as a chiral ligand, furnished optically active 1,4-dibenzyl-2-vinylpiperazine ( 26 ) in 88% yield and 86% ee as described in eqn (1). 21 …”

Section: Catalytic Asymmetric Syntheses Of Carbon-substituted Piperazmentioning

confidence: 99%