Thanks to visit codestin.com
Credit goes to www.scribd.com

Scribd
Upload
58 views3 pages

PROGRESS Unsetisfactory

Rishi Sharma presents a progress report on his research developing novel carbohydrate-based organocatalysts for enantioselective organic reactions. He has done a literature review and synthesized various compounds needed for the research. Key compounds synthesized include tri-O-acetyl-D-glucal and tri-O-benzyl-D-glucal. These were converted into other compounds including a cyclic polyhydroxylated pyrrolidine. Future work involves using this pyrrolidine compound as an organocatalyst in a variety of enantioselective organic reactions in both aqueous and non-aqueous media.

Uploaded by

Jeffery James
Copyright
© Attribution Non-Commercial (BY-NC)
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as DOC, PDF, TXT or read online on Scribd
58 views3 pages

PROGRESS Unsetisfactory

Rishi Sharma presents a progress report on his research developing novel carbohydrate-based organocatalysts for enantioselective organic reactions. He has done a literature review and synthesized various compounds needed for the research. Key compounds synthesized include tri-O-acetyl-D-glucal and tri-O-benzyl-D-glucal. These were converted into other compounds including a cyclic polyhydroxylated pyrrolidine. Future work involves using this pyrrolidine compound as an organocatalyst in a variety of enantioselective organic reactions in both aqueous and non-aqueous media.

Uploaded by

Jeffery James
Copyright
© Attribution Non-Commercial (BY-NC)
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as DOC, PDF, TXT or read online on Scribd
You are on page 1/ 3

Rishi Sharma

2008CYZ8013
Research Scholar

Progress Report
(I Semester of 2009-10)

I have done literature survey related to my research work entitled “Organocatalyst“.

Aim: Major aim of our propose research is to develop some new and novel
carbohydrate based organocatalyst for performing enantioselective organic reactions.

Research work:
The required material for our synthesis namely, tri-O-acetyl-D-
glucal was prepared from D-glucose in two steps as per literature procedure. Acetylation
followed by bromination of D-glucose 1 using acetic anhydride in the presence of
catalytic amount of percholric acid followed by the addition of red phosphorous and
bromine afforded tetra-O-acetyl-D-glucopyranosyl bromide 2, which on reductive
elimination using zinc dust in acidic condition afforded tri-O-acetyl-D-glucal 3. Tri-O-
acetyl-D-glucal was converted into glucal 4 using Na2CO3. Benzylation of 4 has been
done by benzyl chloride in presence of sodium hydride. This tri-O-benzyl-D-glucal 5 in
presence of chloramine-T and catalytic amount of iodine gave product 6. We performed
the reduction of diamine 6 (which was synthesized in one-pot from readily available tri-
O-benzyl-D-glucal) with 1.25 equiv. of LiAlH4 under reflux condition. Reduction was
smoothly achieved to get the product. On exposure to Mitsunobu condition, compound
underwent a smooth cyclisation to afford exclusively the 2-aminomethyl
polyhydroxylated pyrrolidine. In order to obtain compound 9, initially the protected
polyhydroxylated pyrrolidine 8 was treated with Na/Hg to deprotect both the tosyl groups
or either one of them. Interestingly, compound 8 underwent a smooth cleavage of cyclic
tosyl group leading to the formation of compound 8 exclusively in and the secondary
tosyl group remained intact under this condition.

OH OAc
O OAc
HO Ac2O/HClO4 O CH3COONa/gla. AcOH, AcO
AcO O
HO OH AcO
OH Red P + Br2 Zn dust,CuSO4.5H2O AcO
OAc
D-glucose
3 hrs 0 0C, 3 hrs
Br 3
1 2
MeOH,Na2CO3
00C
5h
OBn Chloramine-T,I2,00c, OBn
O NaH,BnCl2,DMF (RT) OH
BnO BnO O O
BnO HO
BnO HO
NHTs CH3CN,16h
NHTs
6 5 4
LAH,THF,680C

OBn OBn
OBn OBn OBn Na-Hg, Na2Po4,3h
PPh3,DEAD (RT)
BnO OH
BnO NHTs N
N NHTsH OBn
NHTs NHTs Ts OBn
7 9
8

Research work to be done

Now we will utilize 9 as an organocatalyst to perform a varity enantioselective organic


reaction both in aqueous and non aqueous media.
Reference:
1. Kumar, V.; Ramesh, N. G. Chem. Commun., 2006, 4952-4954.
2. Seayad, J.; List, B. Org. Biomol.Chem., 2005, 3, 719-724.
3. Nakayama, K.; Maruoka K. J. Am. Chem. Soc., 2008, 130, 17666-17667.
4. Nils, D.; Anders, B.; Hans, A. Adv. Syn. Cat., 2004, 346, 1101-1105.
5. Wei, W.; Jian, W.; Hao, L. Org. Lett., 2004, 6, 2820.

You might also like