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Review
. 2017 May;8(3):245-270.
doi: 10.1016/j.jare.2016.12.005. Epub 2017 Jan 9.

Bis[(l)prolinate-N,O]Zn: A water-soluble and recycle catalyst for various organic transformations

Roona Poddar  1 , Arti Jain  2 , Mazaahir Kidwai  1
Affiliations
Review

Bis[(l)prolinate-N,O]Zn: A water-soluble and recycle catalyst for various organic transformations

Roona Poddar et al. J Adv Res. 2017 May.

Abstract

Under the green chemistry perspective, bis[(l)prolinate-N,O]Zn (also called zinc-proline or Zn[(l)-pro]2) has proven its competence as a promising alternative in a plethora of applications such as catalyst or promoter. Owing to its biodegradable and non-toxic nature of bis[(l)prolinate-N,O]Zn, it is being actively investigated as a water soluble green catalyst for synthetic chemistry. Bis[(l)prolinate-N,O]Zn are readily utilized under mild conditions and have high selectivity and reactivity with broad range of substrate acceptance to make it better reaction medium for a wide variety of organic transformations. This Review summarizes the till date literature on its synthesis, characterization, and its catalytic role in various organic reactions.

Keywords: Amino-acid complex; Asymmetric catalyst; Bis[(l)prolinate-N,O]Zn; Lewis acid; Organometallic chemistry; Zinc.

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Figures

None
Graphical abstract
Scheme 1
Scheme 1
Fig. 1
Fig. 1
1H NMR of proline and bis[(l)prolinate-N,O]Zn.
Fig. 2
Fig. 2
FTIR of bis[(l)prolinate-N,O]Zn.
Fig. 3
Fig. 3
Single crystal X-ray diffraction of bis[(l)prolinateo-N,O]Zn.
Fig. 4
Fig. 4
Powder XRD of bis[(l)prolinate-N,O]Zn.
Fig. 5
Fig. 5
TEM images of fresh bis[(l)prolinate-N,O]Zn.
Fig. 6
Fig. 6
TGA/DTA graph of bis[(l)prolinate-N,O]Zn.
Fig. 7
Fig. 7
DSC graph of bis[(l)prolinate-N,O]Zn.
Scheme 2
Scheme 2
Scheme 3
Scheme 3
Scheme 4
Scheme 4
Scheme 5
Scheme 5
Scheme 6
Scheme 6
Scheme 7
Scheme 7
Fig. 8
Fig. 8
Plausible mechanism for the bis[(l)prolinate-N,O]Zn catalyzed the formation of ribose and other pentoses.
Scheme 8
Scheme 8
Scheme 9
Scheme 9
Fig. 9
Fig. 9
Proposed intermediates for the zinc-supported enamine mechanism of the bis[(l)prolinate-N,O]Zn complex-catalyzed aldol reaction.
Scheme 10
Scheme 10
Scheme 11
Scheme 11
Scheme 12
Scheme 12
Scheme 13
Scheme 13
Scheme 14
Scheme 14
Scheme 15
Scheme 15
Fig. 10
Fig. 10
Ligands that can bind to Zn2+ to form mimic of aldolase enzymes that catalyze stereospecific aldol reactions in a reversible manner.
Fig. 11
Fig. 11
Initially hypothesized scheme for aldol reactions catalyzed by the amino acid part and the Zn2+ ion of the catalyst function in a cooperative manner to generate Zn2+ - enolates.
Scheme 16
Scheme 16
Scheme 17
Scheme 17
Scheme 18
Scheme 18
Scheme 19
Scheme 19
Scheme 20
Scheme 20
Scheme 21
Scheme 21
Fig. 12
Fig. 12
Plausible mechanism for the bis[(l)prolinate-N,O]Zn catalyzed 1,4-addition of terminal alkyne to conjugated enone.
Scheme 22
Scheme 22
Fig. 13
Fig. 13
Proposed mechanism for the preparation of triazoles by the reaction of alkyne, azide and benzyl halides using bis[(l)prolinate-N,O]Zn as a catalyst.
Scheme 23
Scheme 23
Scheme 24
Scheme 24
Fig. 14
Fig. 14
Identification of anti and syn isomers by 1H NMR spectroscopy.
Fig. 15
Fig. 15
Plausible mechanism for the bis[(l)prolinato-N,O]Zn catalyzed reaction for β-aminocarbonyl compounds.
Fig. 16
Fig. 16
Possible transition state leading to anti product.
Scheme 25
Scheme 25
Scheme 26
Scheme 26
Fig. 17
Fig. 17
Enamine(A), Pyrazolone(B).
Scheme 27
Scheme 27
Scheme 28
Scheme 28
Scheme 29
Scheme 29
Fig. 18
Fig. 18
Plausible mechanism for the bis[(l)prolinato-N,O]Zn catalyzed reaction for 4-chromanone derivative compounds.
Scheme 30
Scheme 30
Scheme 31
Scheme 31
Scheme 32
Scheme 32
Fig. 19
Fig. 19
Plausible mechanism for the bis[(l)prolinato-N,O]Zn catalyzed reaction for β-enaminone compounds.
Scheme 33
Scheme 33
Fig. 20
Fig. 20
Plausible mechanism for the bis[(l)prolinate-N,O]Zn catalyzed reaction for thio-Michael reaction.
Scheme 34
Scheme 34
Fig. 21
Fig. 21
Plausible mechanism for the bis[(l)prolinate-N,O]Zn catalyzed 2-amino-4H-benzo[g]chromene by reaction of aldehydes, malononitrile and 2-hydroxy-1,4-naphthaquinone.
Scheme 35
Scheme 35
None
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References

    1. Christiansons W.D., Lipscomb W.N. Carboxypeptidase A. Acc Chem Res. 1992;22:62–69.
    1. Caroline M.L., Kandasamy A., Mohan R., Vasudevan S. Growth and characterization of dichlorobis l-prolineZn(II): a semi organic nonlinear optical single crystal. J Crystal Growth. 2009;311:1161–1165.
    1. Aoki S., Kimura E. Zinc-nucleic acid interaction. Chem Rev. 2004;104:769–787. - PubMed
    1. Yukawa Y., Inomata Y., Takeuchi T., Ouchi M.A.S. The structure of dichloro(4-hydroxy-l-proline)cadmium (II) Bull Chem Soc Jpn. 1982;55:3135–3137.
    1. Yukawa Y., Inomata Y., Takeuchi T. Structure and properties of dichloro(4-hydroxy-l-proline)cadmium (II) hydrate. Bull Chem Soc Jpn. 1983;56:2125–2128.

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