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Chiral Borane-Based Lewis Acids for Metal Free Hydrogenations

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Book cover Chiral Lewis Acids

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 62))

Abstract

The unquenched reactivity of strong Lewis acids in the presence of Lewis bases in solution, the so-called frustrated Lewis pairs (FLP), has led to the discovery of the metal-free activations, whereas the FLP-mediated hydrogen activation is the most prominent. So far, the metal-free hydrogenation is the most studied application of FLP chemistry and highly efficient methodologies for a number of unsaturated substrates have been developed. This chapter starts with a brief introduction to frustrated Lewis pair chemistry. The second part focuses on the synthetic challenges of chiral borane-derived Lewis acids for asymmetric transformations. The last part gives a state-of-the-art summary of asymmetric transformations using chiral FLPs.

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Abbreviations

°C:

Degree Celsius

bar:

Pressure unit, 1.013 mbar, 760 Torr

Bn:

Benzyl

DCM:

Dichloromethane

de:

Diastereomeric excess

dr:

Diastereomeric ratio

ee:

Enantiomeric excess

Et:

Ethyl

FLP:

Frustrated Lewis pair

H2:

Molecular hydrogen, dihydrogen

iPr:

2-Methylethyl

K:

Kelvin

Me:

Methyl

Mes:

Mesitylene, 2,4,6-trimethylphenyl

MTBE:

Methyl-tertbutyl ether

NMR:

Nuclear magnetic resonance

Ph:

Phenyl

PMP:

4-Methoxyphenyl

r.t.:

Room temperature

sBu:

secButyl, 1-methylpropyl

tBu:

1,1-Dimethylethyl

THF:

Tetrahydrofurane

TMP:

2,2,6,6-Tetramethylpiperidine

Tol:

4-Methyl-phenyl

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Authors and Affiliations

  1. Institute of Organic Chemistry, University of Paderborn, Warburger Str. 100, 33098, Paderborn, Germany

    Jan Paradies

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  1. Jan Paradies
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Correspondence to Jan Paradies .

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Editors and Affiliations

  1. Department of Chemical Science and Engineering, School of Materials and Chemical Technology, Tokyo Institute of Technology, Tokyo, Japan

    Koichi Mikami

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Paradies, J. (2017). Chiral Borane-Based Lewis Acids for Metal Free Hydrogenations. In: Mikami, K. (eds) Chiral Lewis Acids. Topics in Organometallic Chemistry, vol 62. Springer, Cham. https://doi.org/10.1007/3418_2016_173

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