-
Novel pyrrolidine-thiohydantoins/thioxotetrahydeopyrimidinones
as highly effective catalysts for the asymmetric Michael
addition
Christoforos G. Kokotos, Dimitris Limnios, Despoina Triggidou,
Maria Trifonidou and George Kokotos*
Laboratory of Organic Chemistry, Department of Chemistry,
University of Athens, Athens 15771, Greece
Supporting Information
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S1
Table of Contents Page 1H and 13C NMR spectra S2
HPLC data
Structures of enamine intermediates
S25
S35
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S2
NBoc
NH
NH
S
OMe
Ph O
9
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S3
NH
NH
S O
OMe
Ph
Ph
NHBoc
Ph
11
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S4
12
NH
N
NH
S Ph
O
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S5
Ph
Ph
NH2
NNH
O
S
Ph
13
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S6
15a
NBoc
NH
NH
SOMe
O
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S7
15b
NBoc
NH
NH
SOMe
O
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S8
15cNBoc
NH
NH
SOMe
O
CH2Ph
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S9
15d
NBoc
NH
NH
SOMe
O
Ph
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S10
15eNBoc
NH
NH
SOMe
O
Ph
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S11
16a
NH
N
NH
O
S
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S12
16b
NH
N
NH
O
S
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S13
16c
NH
N
NH
O
SCH2Ph
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S14
16d
NH
N
NH
O
SPh
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S15
16e
NH
N
NH
O
SPh
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S16
NBoc
N
NH
S Ph
O
17
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S17
ONO2
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S18
N
ONO2
Ac
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S19
ONO2
ONO2
O
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S20 F
ONO2
ONO2
NO2
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S21
ONO2
OMe
ONO2
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S22
O
ONO2
S
ONO2
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S23
ONO2
O O
ONO2
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S24
N
ONO2
Ac
syn:anti 53:47
Reaction with organocatalyst 7a
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S25
ONO2
ONO2
O
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S26
ONO2
F
ONO2
NO2
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S27
ONO2
OMe
ONO2
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S28
racemic
S
ONO2
S
ONO2
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S29
racemic
ONO2
ONO2
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
-
C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S30
racemic
O O
ONO2
O O
ONO2
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S31
racemic
N
ONO2
Ac
N
ONO2
Ac
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S32
O
ONO2
O
NO2
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S33
ONO2
HMe
ONO2
Me
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S34
HBn
ONO2
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S35
enamine of catalyst 12 enamine of catalyst 16e
enamine of catalyst 16d enamine of catalyst 16a
Maestro 9.1 Macromodel
Force field: OPLS_2005
Solvent: CHCl3
Electrostatic treatment: Constant dielectric
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou & G.
Kokotos Supporting Information S36
Dielectric constant: 1.0
Charges from: Force field
Cutoff: Extended
Method: PRCG
Max. iterations: 5000
Converge on: Gradient
Convergethreshold: 0.01
Supplementary Material (ESI) for Organic & Biomolecular
ChemistryThis journal is (c) The Royal Society of Chemistry
2011
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