PRESENTED BY:- UNDER THE SUPERVISION

SUSHREE SUMAN DASH OF:-

M.Sc INDUSTRIAL Dr. RAMAKRISHNA D.S.
CHEMISTRY Assistant Professor
REGD.NO. 1707120007
DEPARTMENT OF CHEMISTRY
VSSUT, BURLA
CONTENTS
 INTRODUCTION
 PROLINE
 PROLINAMIDE
 PROLINE DIPEPTIDE WITH FLUORINE MOIETY
 TRIPEPTIDE
 β-AMINOSULFONAMIDE
 ACHIRAL ISOTHIOURONIUM IODIDE
 DIARYLPROLINOL
 PPLII
 PYRROLIDINE-DIAMINOMETHYLENEMALONITRILE
 CONCLUSION
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INTRODUCTION:
β-hydroxy carbonyl functional group is a common structural feature in many
natural products.

The organocatalysts are divided into 9 categories as shown below:

1. 2. 3.

4. 5. 6.

7. 8. Enzymes such as PPLII 9.

and AUAP (acidic protease
from aspergillus usamii).

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1. PROLINE:
The initial research work in the field of organocatalysis based on asymmetric aldol
reaction using L-Proline was reported by Hajos-Parrish-Eder-Sauer-Weichert in the year
1974.

PROLINE CATALYZED ASYMMETRIC ALDOL REACTION:

Usman I. Tafida reported a possible mechanism for asymmetric aldol reaction between
acetone and p-nitrobenzaldehyde in acetone medium in the year 2018.

MECHANISM:

1.a)Usman I. Tafida, Adamu Uzairu and Stephen E. Abechi , J.Adv.Research, 2018, 12, 11-19.
b)Zoltan G. Hajos,and David R. Parrish J., Org. chem; 1974, 39, 1615-1621. 2
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2. PROLINAMIDE:
Moutevelis-Minakakis and co workers identified the combination of prolinamide
consisting of phenyl alanine in the year 2018.

3. PROLINE DIPEPTIDE WITH FLUORINE MOIETY:

This catalyst worked well in room temperature and the reaction was carried out in wet
petroleum ether media.

2.Ismini Vlasserou, Maria Sfetsa, Dimitrios-Triantafyllos Gerokonstantis, Christoforos G. Kokotos and Panagiota Moutevelis-Minakakis,
Tetrahedron, 2018, 74, 2338-2349.
3. Ardiol Ahmetlli, Nikoleta Spiliopoulou, Angeliki Magi-Oikonomopoulou, Dimitrios-Triantaffylos, Gerokonstantis, Panagiota Moutevelis- 3
Minakaki and, Christoforos G. Kokotos, Tetrahedron, 2018, 74, 5987-5995.
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4. TRIPEPTIDE: The catalyst worked well in both aqueous and organic medium.

5. β-AMINOSULFONAMIDE: The reaction is carried out in presence of water and a

moderate to excellent yield is obtained.

4. Anastasia Psarra, Christoforos G. Kokotos, and Panagiota Moutevelis-Minakakis, Tetrahedron, 2014,70, 608-615.
5. Tsuyoshi Miura, Mariko Ina, Kie Imai, Kosuke Nakashima, Yumi Yasaku, Naka Koyata, Yasuoki Murakami, Nobuyuki Imai,
Norihiro Tada, and Akichika Itoh, Tetrahedron, 2011, 22, 1028-1034.
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6. ACHIRAL ISOTHIOURONIUM IODIDE: The catalyst worked well with just 20 mol%
loading in the absence of solvent inside a refrigerator without stirring for about 96h.

7. DIARYLPROLINOL: The reaction gave good results in presence of THF as solvent.

6. Eun cho and, Taek Hyeon Kim, Tetrahedron lett., 2014, 55, 6470-6473.
7. Yujiro Hayashi, and Masahiro Kojima, Chemcatchem, 2013, 47, 2713-2717.
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8. PPLII: The method being biocatalytic proved to be green.

9. PYRROLIDINE-DIAMINOMETHYLENEMALONITRILE: The catalyst worked well under

solvent free conditions.

8. Zho Guan, Jian Ping Fu, and Yan-Hong He, Tetrahedron lett. 2012, 53, 4959-4961.
9. Kosuke Nakashima , Shin-Ichi Hirashima, Hiroshi Akutsu, Yuji Koseki, Norihiro Tada, Akichika Itoh, and Tsuyoshi Miura,
Tetrahedron lett., 2015, 56, 558-561.
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CONCLUSION:
1.Some methods result in high enantiomeric
excess upto 99% and even diastereomeric
ratio upto 99% under milder conditions.
2. Green solvents such as water and ionic liquid
are used for this purpose.
3.Methods are highly selective in quenching the
process resulting in β-hydroxy ketones as
major products and prevents aldol
condensation products.