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C-C Bond Activation pp 163–193Cite as

Asymmetric Transformations via C–C Bond Cleavage

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Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 346))

Abstract

Catalytic asymmetric transformations operating by carbon–carbon (C–C) bonds cleavages have emerged as intriguing strategies to access transient organometallic species from different reaction pathways. The reactions and the applicable substrate range have expanded considerably over the last decade. This overview covers the main developments in this field. A major focus is placed on β-carbon eliminations of strained tert-alcohols and related processes which have been shown to be particularly versatile in a broad range of transformations. Furthermore, exciting developments of asymmetric processes based on direct oxidative C–C bond insertion reactions, for instance into the acyl C–C bond of ketones or the C–CN bond of nitriles, are discussed.

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Abbreviations

acac:

Acetylacetonate

Ac:

Acetyl

Alk:

Alkyl

Ar:

Aryl

BARF:

Tetrakis(3,5-bis(trifluoromethyl)phenyl)borate

Binap:

2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl

Bn:

BENZYL

cod:

Cyclooctadiene

Cp:

Cyclopentadienyl

d:

Day(s)

dba:

Tris(dibenzylideneacetone)

dppb:

1,4-Bis(diphenylphosphino)butane

dr:

Diastereomer ratio

DCE:

Dichloroethane

DME:

Dimethoxy ethane

DMF:

Dimethyl formamide

DMPU:

1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone

DTBM:

3,5-Di-tert-butyl-4-methoxyphenyl

ee :

Enantiomeric excess

equiv:

Equivalent(s)

Et:

Ethyl

h:

Hour(s)

iPr:

Isopropyl

L:

Ligand

LA:

Lewis acid

mol:

Mole(s)

M:

Metal

Me:

Methyl

Mes:

Mesityl, 2,4,6-trimethylphenyl

MS:

Molecular sieve

Np:

Naphthyl

Ph:

Phenyl

PMB:

4-Methoxyphenyl

quant:

Quantitative

tBu:

tert-butyl

tert :

Tertiary

TBS:

tert-Butyldiphenylsilyl

Tol:

4-Methylphenyl

Ts:

Tosyl, 4-toluenesulfonyl

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  1. Laboratory of Asymmetric Catalysis and Synthesis, Institute of Chemical Sciences and Engineering, School of Basic Sciences, Ecole Polytechnic Fédérale de Lausanne, 1015, Lausanne, Switzerland

    Laetitia Souillart, Evelyne Parker & Nicolai Cramer

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  1. Laetitia Souillart
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  2. Evelyne Parker
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  3. Nicolai Cramer
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Correspondence to Nicolai Cramer .

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  1. The University of Texas at Austin Department of Chemistry & Biochemistry, Austin, USA

    Guangbin Dong

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© 2014 Springer-Verlag Berlin Heidelberg

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Souillart, L., Parker, E., Cramer, N. (2014). Asymmetric Transformations via C–C Bond Cleavage. In: Dong, G. (eds) C-C Bond Activation. Topics in Current Chemistry, vol 346. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2013_505

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