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Frustrated Lewis Pair Catalyzed Asymmetric Reactions

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Frustrated Lewis Pairs

Part of the book series: Molecular Catalysis ((MOLCAT,volume 2))

Abstract

As a lately emerging area, frustrated Lewis pair chemistry provides the most effective way for metal-free catalytic reductions, and a wide range of unsaturated compounds have been successfully reduced. However, the asymmetric catalytic reduction is still in its initial stage, and some formidable challenges still remain. The development of highly effective chiral FLP catalysts and their applications in asymmetric catalysis are two very important subjects in this field. This chapter will summarize the advances for chiral FLP catalysts and metal-free asymmetric reductions including hydrogenations, Piers-type hydrosilylations, and transfer hydrogenations in the past six years.

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Abbreviations

Ac:

Acetyl

Ar:

Aryl

Atm:

Atmosphere

Barton’s base:

2-tert-butyl-1,1,3,3-tetramethylguanidine

Bn:

Benzyl

Boc:

t-Butyloxy carbonyl

Bu:

Butyl

Cat.:

Catalyst

Cbz:

Benzyloxycarbonyl

Conv.:

Conversion

Cy:

Cyclohexyl

DCM:

Dichloromethane

DFT:

Density Functional Theory

DIBAL-H:

Diisobutyl aluminium hydride

DMF:

Dimethylformamide

DMS:

Dimethyl sulfide

dr:

Diastereomeric ratio

ee:

Enantiomeric excess

equiv.:

Equivalent(s)

Et:

Ethyl

FLPs:

Frustrated Lewis pairs

LA:

Lewis acid

LB:

Lewis base

Me:

Methyl

Mes:

2,4,6-Trimethylphenyl

NHC:

N-heterocyclic carbene

Np:

Naphthyl

PCC:

Pyridinium chlorochromate

Ph:

Phenyl

Piers’ Borane:

HB(C6F5)2

Pin:

Pinacol

PG:

Protecting group

PMHS:

Polymethylhydrosiloxane

PMP1:

p-Methoxyphenyl

PMP2:

1,2,2,6,6-Pentamethylpiperidine

Pr:

Propyl

Rt:

Room temperature

TBAF:

Tetrabutylammonium fluoride

Tf:

Trifluoromethylsulfonate

THF:

Tetrahydrofuran

TMS:

Trimethylsilyl

Tol:

Tolyl

Ts:

Tosyl

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Authors and Affiliations

  1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China

    Xiangqing Feng, Wei Meng & Haifeng Du

  2. University of Chinese Academy of Sciences, Beijing, 100049, China

    Xiangqing Feng, Wei Meng & Haifeng Du

Authors
  1. Xiangqing Feng
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  2. Wei Meng
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  3. Haifeng Du
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Correspondence to Haifeng Du .

Editor information

Editors and Affiliations

  1. Van ‘t Hoff Institute for Molecular Sciences, University of Amsterdam, Amsterdam, The Netherlands

    J. Chris Slootweg

  2. School of Chemistry, University of Birmingham, Edgbaston, UK

    Andrew R. Jupp

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Feng, X., Meng, W., Du, H. (2021). Frustrated Lewis Pair Catalyzed Asymmetric Reactions. In: Chris Slootweg, J., Jupp, A.R. (eds) Frustrated Lewis Pairs. Molecular Catalysis, vol 2. Springer, Cham. https://doi.org/10.1007/978-3-030-58888-5_2

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