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Progress in Chemistry 2022, Vol. 34 Issue (7): 1537-1547 DOI: 10.7536/PC220221 Previous Articles   Next Articles

• Review •

Condensed Matter Chemistry in Asymmetric Catalysis and Synthesis

Ru Jiang, Chenxu Liu, Ping Yang, Shuli You()   

  1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences,Shanghai 200032, China
  • Received: Revised: Online: Published:
  • Contact: Shuli You
  • Supported by:
    National Natural Science Foundation of China(91856201)
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Condensed matter chemistry, as a science of studying condensed matter in chemical reactions, has attracted extensive attention recently. In this review, condensed matter chemistry related to asymmetric catalysis and synthesis are briefly summarized, and different condensed matter phenomena in asymmetric catalytic reactions were classified. Besides, relative works were discussed in detail to illustrate the effects of the multi-level structures and composition of condensed matter on the catalytic activity, enantio- and regioselective control. It is hoped that the system of condensed matter science would be well developed by attracting more attention and bringing more thoughts to the essence of reaction from the perspective of condensed matter chemistry.

Contents

1 Introduction

2 Chirality and asymmetric catalysis

2.1 Importance of chirality

2.2 Asymmetric catalysis

3 Condensed matter chemistry in asymmetric catalysis and synthesis

3.1 Condensation of catalysts: nonlinear effect

3.2 Condensation of catalysts and solvents

3.3 Condensation of catalysts and additives

3.4 Condensation of catalysts and substrates: phase-transfer catalysis

3.5 Condensation of enantiomers: SDE

4 Conclusion and outlook

Key words: condensed state, asymmetric catalysis, enantioselectivity, nonlinear effect, solvent effect, phase-transfer catalysis, self-disproportionation of enantiomers
Fig. 1 Nonlinear effects in asymmetric catalysis and synthesis[5]
Scheme 1 Highly enantioselective addition of dialkylzincs to aldehydes[7]
Scheme 2 Reaction mechanism[8]
Scheme 3 Asymmetric amplification and related mechanism[8⇓~10]
Scheme 4 (l)-Proline-catalyzed asymmetric reactions[11,12]
Fig. 2 Nonlinearity of proline catalysis under heterogeneous conditions[13]
Scheme 5 Time-dependent enantiodivergent synthesis via sequential kinetic resolution[16,17]
Scheme 6 Iridium-catalyzed Z-retentive asymmetric allylic substitution reactions[17]
Scheme 7 Synthesis and characterization of π-allyl iridium(Ⅲ) complexes[18]
Table 1 Enantioselective Friedel-Crafts reaction between indoles and alkylidene malonates catalyzed by copper(Ⅱ) complexes[25,26]
entry Ligand/Cu solvent temperature
(℃)		 time (h) yield
(%)		 ee
1 1/1.5 CHCl2CHCl2 0 22 86 80% (R)
2 1.2/1 THF 15 64 5 81% (S)
3 1.2/1 MeOH 15 5 90 48% (S)
4 1.2/1 EtOH 15 3 90 63% (S)
5 1.2/1 iPrOH 15 2 99 88% (S)
6 1.2/1 iBuOH 15 3 99 90% (S)
Fig. 3 Stereochemical models[26]
Scheme 8 Orthogonal enantioselectivity approaches using homogeneous and heterogeneous catalyst systems: Friedel-Crafts alkylation of indole[28]
Fig. 4 Proposed stereochemical models for (a) homogeneous, and (b) heterogeneous systems[28]
Fig. 5 Chiral cation phase-transfer catalyst[32]
Fig. 6 Mechanism of chiral cation phase-transfer catalysis reaction[32]
Scheme 9 The first example of phase-transfer catalysis[33]
Fig. 7 Mechanism of cyanation reaction via chiral phase-transfer catalysis[33]
Scheme 10 The first example of asymmetric phase-transfer catalysis reaction[34]
Scheme 11 Asymmetric electrophilic fluorination via chiral anion phase-transfer catalysis[35]
Fig. 8 Mechanism of chiral anion phase-transfer catalysis reaction[35]
Fig. 9 The principle of enantiomeric self-disproportionation[37]
Table 2 Self-disproportionation of enantiomers of β-amino acid esters on achiral silica gel chromatography[36]
Compound Starting ee (%) Eluent ee (%) min ee (%) max
A 95.0 Hex/EtOAc = 5∶1 83.3 99.9
31.1 Hex/EtOAc = 5∶1 20.9 41.8
66.6 Hex/EtOAc = 5∶1 8.1 99.9
66.6 Hex/E2O = 1∶1 54.8 99.9
66.6 CHCl3 65.5 68.2
B 66.6 Hex/EtOAc = 5∶1 58.4 99.9
C 66.6 Hex/EtOAc = 5∶1 59.9 78.8
Fig. 10 Self-disproportionation of enantiomers on achiral silica gel chromatography[36,39]
Fig. 11 Packing structure of racemic 1, 2-dihydroisoquinolines derivative[39]
Fig. 12 Self-disproportionation of enantiomers during distillation[42]
Fig. 13 Self-disproportionation of enantiomers during sublimation[43,44]
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