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. 2007 Feb 1;9(3):457-60.
doi: 10.1021/ol062808f.

Mild conditions for the synthesis of functionalized pyrrolidines via Pd-catalyzed carboamination reactions

Myra Beaudoin Bertrand  1 , Matthew L Leathen, John P Wolfe
Affiliations

Mild conditions for the synthesis of functionalized pyrrolidines via Pd-catalyzed carboamination reactions

Myra Beaudoin Bertrand et al. Org Lett. .

Abstract

[reaction: see text] The palladium-catalyzed carboamination of N-protected gamma-aminoalkenes with aryl bromides and triflates has been achieved under new, mild reaction conditions using the weak base Cs(2)CO(3) in dioxane solvent. These reactions tolerate a wide variety of functional groups, including enolizable ketones, nitro groups, methyl esters, and acetates, which are not compatible with previously described conditions.

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Figures

Scheme 1
Scheme 1
Stereoselective Synthesis of 25
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References

    1. For recent reviews, see: Bellina F, Rossi R. Tetrahedron. 2006;62:7213–7256. Coldham I, Hufton R. Chem. Rev. 2005;105:2765–2810.

    1. Ney JE, Wolfe JP. Angew. Chem., Int. Ed. 2004;43:3605–3608. - PubMed
    2. Lira R, Wolfe JP. J. Am. Chem. Soc. 2004;126:13906–13907. - PubMed
    3. Bertrand MB, Wolfe JP. Tetrahedron. 2005;61:6447–6459.
    4. Ney JE, Wolfe JP. J. Am. Chem. Soc. 2005;127:8644–8651. - PMC - PubMed
    5. Yang Q, Ney JE, Wolfe JP. Org. Lett. 2005;7:2575–2578. - PMC - PubMed
    6. Ney JE, Hay MB, Yang Q, Wolfe JP. Adv. Synth. Catal. 2005;347:1614–1620. - PMC - PubMed
    7. Bertrand MB, Wolfe JP. Org. Lett. 2006;8:2353–2356. - PMC - PubMed

    1. For a review on other Pd-catalyzed alkene carboamination reactions that afford pyrrolidine products, see: Wolfe JP. Eur. J. Org. Chem. 2007 in press. See also:Harayama H, Abe A, Sakado T, Kimura M, Fugami K, Tanaka S, Tamaru Y. J. Org. Chem. 1997;62:2113–2122. Scarborough CC, Stahl SS. Org. Lett. 2006;8:3251–3254. Sherman ES, Chemler SR, Tan TB, Gerlits O. Org. Lett. 2004;6:1573–1575. Larock RC, Yang H, Weinreb SM, Herr RJ. J. Org. Chem. 1994;59:4172–4178.

    1. Dpe-phos = bis(2-diphenylphosphinophenyl)ether.

    1. The use of Cs2CO3 and other weak bases in Pd-catalyzed N-arylation reactions of amines with aryl halides has been reported. For reviews, see: Muci AR, Buchwald SL. Top. Curr. Chem. 2002;219:131–209. Hartwig JF. In: Modern Arene Chemistry. Astruc D, editor. Wiley, VCH; Weinheim: 2002. pp. 107–168. Schlummer B, Scholz U. Adv. Synth. Catal. 2004;346:1599–1626.

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