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Amine, Alcohol and Phosphine Catalysts for Acyl Transfer Reactions

Part of the Topics in Current Chemistry book series (TOPCURRCHEM,volume 291)

Abstract

An overview of the area of organocatalytic asymmetric acyl transfer processes is presented including O- and N-acylation. The material has been ordered according to the structural class of catalyst employed rather than reaction type with the intention to draw mechanistic parallels between the manner in which the various reactions are accelerated by the catalysts and the concepts employed to control transfer of chiral information from the catalyst to the substrates.

Keywords

  • Acylation
  • Asymmetric desymmetrisation
  • Esterification
  • Kinetic resolution
  • Nucleophilic catalysis

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Scheme 1
Scheme 2
Scheme 3
Fig. 1
Fig. 2
Scheme 4
Fig. 3
Scheme 5
Fig. 4
Fig. 5
Scheme 6
Scheme 7
Scheme 8
Scheme 9
Scheme 10
Fig. 6
Scheme 11
Scheme 12
Fig. 7
Scheme 13
Fig. 8
Scheme 14
Fig. 9
Fig. 10
Fig. 11
Scheme 15
Scheme 16
Scheme 17
Scheme 18
Scheme 19
Fig. 12
Scheme 20
Scheme 21
Fig. 13
Fig. 14
Scheme 22
Scheme 23
Scheme 24
Fig. 15
Fig. 16
Scheme 25

Abbreviations

Ac:

Acetyl

Alloc:

Allyloxycarbonyl

ASD:

Asymmetric desymmetrization

Bn:

Benzyl (CH2Ph)

Boc:

Tert-butoxycarbonyl

C:

Conversion

Cat:

Catalyst

Cbz:

Benzyloxycarbonyl

Cy:

Cyclohexyl

(DHQ)2AQN:

Hydroquinine anthraquinone-1,4-diyl diether

(DHQD)2AQN:

Hydroquinidine anthraquinone-1,4-diyl diether

4-DMAP:

4-(Dimethylamino)pyridine

E:

Electrophile

ee :

Enantiomeric excess

ent :

Enantiomeric

er :

Enantiomeric ratio

Fmoc:

9-Fluorenylmethyloxylacrbonyl

GABA:

γ-Aminobutyric acid

GC:

Gas chromatography

HPLC:

High pressure liquid chromatography

KR:

Kinetic resolution

MS:

molecular seives

N/A:

Not available

Nap:

Naphthyl

NHC:

N-heterocyclic carbenes

NMR:

Nuclear magnetic resonance

nOe:

nuclear Overhauser effect

Nu:

Nucleophile

PBO:

P-aryl-2-phosphabicyclo[3.3.0]octane

Phe:

(S)-Phenylalanyl

PIP:

2-Phenyl-2,3-dihydroimidazo[1,2a]pyridine

PIQ:

2-Phenyl-1,2-dihydroimidazo[1,2a]quinoline

PKR:

Parallel KR

4-PPY:

4-(Pyrrolidino)pyridine

rec SM:

Recovered starting material

s :

Selectivity factor

sec :

Secondary

TADMAP:

3-(2,2,-Triphenyl-1-acetoxyethyl)-4-dimethylamino)pyridine

TBDPS:

Tert-butyldiphenylsilyl

TBS:

Tert-butyldimethylsilyl

TES:

Triethylsilyl

TFA:

Trifluoroacetic acid

Trt:

Trityl (triphenylmethyl)

UNCA:

Urethane-protected α-amino acid N-carboxy anhydride

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Spivey, A.C., Arseniyadis, S. (2010). Amine, Alcohol and Phosphine Catalysts for Acyl Transfer Reactions. In: List, B. (eds) Asymmetric Organocatalysis. Topics in Current Chemistry, vol 291. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-02815-1_25

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