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Allylic Substitutions Catalyzed by Miscellaneous Metals

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Transition Metal Catalyzed Enantioselective Allylic Substitution in Organic Synthesis

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 38))

Abstract

Allylic substitutions catalyzed by miscellaneous metals have recently been uncovered as useful alternatives to the established corresponding transition metal catalyzed transformations. In particular, the interesting regioselectivity course of the allylic substitutions is of synthetic interest. In this chapter, we summarize the most recent findings in the field of group 8–10 metal (Fe, Ru, Co, Rh, Ni, Pt) catalyzed substitutions with a strong emphasis on the substrate range and the regioselectivity.

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Abbreviations

Ac:

Acetyl

acac:

Acetylacetonate

Alk:

Alkyl

Ar:

Aryl

bmim:

Butylmethylimidazolium

Boc:

tert-Butyloxycarbonyl

cat:

Catalytic

cod:

Cyclooctadiene

Cp:

Cyclopentadienyl

Cp*:

Pentamethylcyclopentadienyl

DCE:

1,2-Dichloroethane

DCM:

Dichloromethane

DMA:

N,N-Dimethylacetamide

DME:

1,2-Dimethoxyethane

DMF:

N,N-Dimethylformamide

DMM:

Dimethylmalonate

DPM:

Bis(diphenylphosphino)methan

dppe:

Bis(diphenylphosphino)ethane

dppf:

Bis(diphenylphosphino)ferrocene

dr:

Diastereomeric ratio

en:

1,2-Ethylenediamine

equiv:

Equivalent(s)

Et:

Ethyl

FG:

Functional Group

h:

Hour(s)

i-Bu:

iso-Butyl

i-Pr:

iso-Propyl

LG:

Leaving group

Mbs:

N-4-Methoxybenzenesulfonyl toluidin

Me:

Methyl

Mes:

Mesityl

min:

Minute(s)

mol:

Mole(s)

MTBE:

tert-Butylmethylether

NHC:

N-Heterocyclic carbene

NMP:

N-Methyl-pyrrolidinon

Nu:

Nucleophile

Pent:

Pentyl

Ph:

Phenyl

Pin:

Pinacol

pip:

Piperidinium

PMP:

p-Methoxyphenyl

rt:

Room temperature

S N :

Nucleophilic Substitution

TBAF:

Tetrabutylammonium fluoride

t-Bu:

tert-Butyl

Tfa:

Trifluoroacetic acid

THF:

Tetrahydrofuran

tmeda:

N,N,N′,N′-Tetramethyl-1,2-ethylenediamine

TMS:

Trimethylsilyl

TsOH:

Toluenesulfonic acid

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Authors and Affiliations

  1. Institute of Organic Chemistry, University of Stuttgart, Pfaffenwaldring 55, 70569, Stuttgart, Germany

    Jeanne-Marie Begouin, Johannes E. M. N. Klein, Daniel Weickmann & Bernd Plietker

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  1. Jeanne-Marie Begouin
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  2. Johannes E. M. N. Klein
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  3. Daniel Weickmann
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  4. Bernd Plietker
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Correspondence to Bernd Plietker .

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  1. Inst. Organische Chemie, Universität des Saarlandes, Gebäude C 4.2, Saarbrücken, 66123, Germany

    Uli Kazmaier

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Begouin, JM., Klein, J.E.M.N., Weickmann, D., Plietker, B. (2011). Allylic Substitutions Catalyzed by Miscellaneous Metals. In: Kazmaier, U. (eds) Transition Metal Catalyzed Enantioselective Allylic Substitution in Organic Synthesis. Topics in Organometallic Chemistry, vol 38. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3418_2011_15

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