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Preparation of Organoalanes for Organic Synthesis

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Modern Organoaluminum Reagents

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 41))

Abstract

Organoaluminums have become more and more important in organic synthesis due to their excellent reactivity and chemoselectivity. Several methods are available for the preparation of various organoaluminums: transmetalation of organomagnesium or lithium reagents, direct insertion of aluminum powder, deprotonation reactions using aluminate bases (metalation), hydro- and carboalumination of unsaturated compounds, and cycloaddition reactions. These methods provide access to aryl, alkynyl, alkenyl, alkyl, allylic, benzylic, and propargylic organoaluminums which all have interesting properties, and can be readily used in organic synthesis.

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Abbreviations

acac:

Acetyl acetonate

Bn:

Benzyl

Bu:

Butyl

c-Hex:

Cyclohexyl

CuTC:

Copper thiophenecarboxylate

dba:

Dibenzylideneacetone

DIBAL-H:

Diisobutylaluminiumhydride

dppe:

1,2-Bis(diphenylphosphino)ethane

dr:

Diastereomeric ratio

ee:

Enantiomeric excess

Hex:

Hexyl

iBu:

iso-Butyl

iPr:

iso-Propyl

M:

Molar

NMI:

Neomenthylindenyl

NMP:

N-Methyl-2-pyrrolidone

NMR:

Nuclear Magnetic Resonance

OAc:

Acetate

PEPPSI:

[1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride

PMDTA:

N,N,N',N',N"-Pentamethyldiethylenetriamine

TMP:

2,2,6,6-Tetramethylpiperidyl

ttmpp:

Tris(2,4,6-trimethoxyphenyl)phosphine

ZACA:

Zirconium-catalyzed asymmetric carboalumination

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Author information

Authors and Affiliations

  1. Department of Chemistry, Ludwig-Maximilians-Universität, Butenandtstr. 5-13, Building F, 81377, Munich, Germany

    Paul Knochel, Tobias Blümke, Klaus Groll & Yi-Hung Chen

Authors
  1. Paul Knochel
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  2. Tobias Blümke
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  3. Klaus Groll
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  4. Yi-Hung Chen
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Corresponding author

Correspondence to Paul Knochel .

Editor information

Editors and Affiliations

  1. , School of Chemistry, The University of Nottingham, University Park, Nottingham, NG7 2RD, United Kingdom

    Simon Woodward

  2. Laboratoire DECOMET, Institut Le Bel, Université de Strasbourg, 4 rue Blaise Pascal, Strasbourg, 67000, France

    Samuel Dagorne

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© 2012 Springer-Verlag Berlin Heidelberg

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Knochel, P., Blümke, T., Groll, K., Chen, YH. (2012). Preparation of Organoalanes for Organic Synthesis. In: Woodward, S., Dagorne, S. (eds) Modern Organoaluminum Reagents. Topics in Organometallic Chemistry, vol 41. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3418_2012_36

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