Organocatalytic Enantioselective Conjugate Addition of ...
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S1 Organocatalytic Enantioselective Conjugate Addition of Pyrazolin-5-ones to Arylomethylidene Malonates Arun Sharma, Vivek Sharma, Swapandeep Singh Chimni* Department of Chemistry Guru Nanak Dev University Amritsar-143005, Punjab, India S.No. Page no. 1. 1 H and 13 C spectra of compound 1a–5a S2–S44 2. HPLC chromatograms of compound 3a–5a S45–S72 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is © The Royal Society of Chemistry 2019
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Transcript of Organocatalytic Enantioselective Conjugate Addition of ...
S1
Organocatalytic Enantioselective Conjugate Addition of
Pyrazolin-5-ones to Arylomethylidene Malonates
Arun Sharma, Vivek Sharma, Swapandeep Singh Chimni*
Department of Chemistry Guru Nanak Dev University Amritsar-143005, Punjab, India
S.No. Page no.
1. 1H and 13C spectra of compound 1a–5a S2–S44
2. HPLC chromatograms of compound 3a–5a S45–S72
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2019
S2
O
COOEt
COOEt
1a
O
COOEt
COOEt
1a
S3
O
COOEt
COOEtCl
1b
O
COOEt
COOEtCl
1b
S4
O
COOEt
COOEtBr
1c
O
COOEt
COOEtBr
1c
S5
O
COOEt
COOEt
F 1d
O
COOEt
COOEt
F 1d
S6
O
COOEt
COOEt
1eBr
O
COOEt
COOEt
1eBr
S7
O
COOEt
COOEt
Br 1e
O
COOEt
COOEt
Br 1e
S8
O
COOEt
COOEt
1fCl
Br
O
COOEt
COOEt
1fCl
Br
S9
O
COOEt
COOEtOMe
1g
O
COOEt
COOEtOMe
1g
S10
O
COOEt
COOEtMeO
1h
O
COOEt
COOEtMeO
1h
S11
O
COOEt
COOEt
MeO 1i
O
COOEt
COOEt
MeO 1i
S12
O
COOEt
COOEt
H3C 1j
O
COOEt
COOEt
H3C 1j
S13
O
COOEt
COOEtO2N
1k
O
COOEt
COOEtO2N
1k
S14
O
COOEt
COOEt
1i
O
COOEt
COOEt
1i
S15
O
COOEt
COOEt
S 1m
O
COOEt
COOEt
S 1m
S16
O
COOEt
COPh
4
O
COOEt
COPh
4
S17
O
COOEt
COOEt
N N
OAc
Ph3a
O
COOEt
COOEt
N N
OAc
Ph3a
S18
O
COOEt
COOEt
N N
OAc
Ph
Cl
3b
O
COOEt
COOEt
N N
OAc
Ph
Cl
3b
S19
O
COOEt
COOEt
N N
OAc
Ph3c
Br
O
COOEt
COOEt
N N
OAc
Ph3c
Br
S20
O
COOEt
COOEt
N N
OAc
Ph
F
3d
O
COOEt
COOEt
N N
OAc
Ph
F
3d
S21
O
COOEt
COOEt
N N
OAc
Ph
Br
3e
O
COOEt
COOEt
N N
OAc
Ph
Br
3e
S22
O
COOEt
COOEt
ClN N
OAc
Br
Ph1f
O
COOEt
COOEt
ClN N
OAc
Br
Ph1f
S23
O
COOEt
COOEt
N N
OAc
Ph
OMe
3g
O
COOEt
COOEt
N N
OAc
Ph
OMe
3g
S24
O
COOEt
COOEt
N N
OAc
Ph
MeO
3h
O
COOEt
COOEt
N N
OAc
Ph
MeO
3h
S25
O
COOEt
COOEt
N N
OAc
Ph3i
MeO
O
COOEt
COOEt
N N
OAc
Ph3i
MeO
S26
O
COOEt
COOEt
N N
OAc
Ph
Me
3j
O
COOEt
COOEt
N N
OAc
Ph
Me
3j
S27
O
COOEt
COOEt
N N
OAc
Ph
O2N
3k
O
COOEt
COOEt
N N
OAc
Ph
O2N
3k
S28
O
COOEt
COOEt
N N
OAc
Ph3l
O
COOEt
COOEt
N N
OAc
Ph3l
S29
O
COOEt
COOEt
N N
OAc
Ph
S
3m
O
COOEt
COOEt
N N
OAc
Ph
S
3m
S30
O
COOEt
COOEt
N N
OAc
Ph
F3C3n
O
COOEt
COOEt
N N
OAc
Ph
F3C3n
S31
O
COOEt
COOEt
N N
OAc
Ph3o
O
COOEt
COOEt
N N
OAc
Ph3o
S32
O
COOEt
COOEt
N N
OAc
Ph
Ph
3p
O
COOEt
COOEt
N N
OAc
Ph
Ph
3p
S33
O
COOEt
COOEt
N N
OAc
Ph
PhMeO
3q
O
COOEt
COOEt
N N
OAc
Ph
PhMeO
3q
S34
O
COOEt
COOEt
N N
OAc
Ph
Ph
MeO
3r
O
COOEt
COOEt
N N
OAc
Ph
Ph
MeO
3r
S35
O
COOEt
COOEt
N N
OAc
Ph
F3CMeO
3s
O
COOEt
COOEt
N N
OAc
Ph
F3CMeO
3s
S36
O
COOEt
COOEt
N N
OAc
Ph
F3CS
3t
O
COOEt
COOEt
N N
OAc
Ph
F3CS
3t
S37
O
COOEt
COOEt
N N
OAc
Ph3u
MeO
O
COOEt
COOEt
N N
OAc
Ph3u
MeO
S38
O
COOEt
COOEt
N N
OAc
Ph
F
3v
O
COOEt
COOEt
N N
OAc
Ph
F
3v
S39
O
COOEt
COOEt
N N
OAc
Ph3w
MeO
O
COOEt
COOEt
N N
OAc
Ph3w
MeO
S40
O
COOEt
COOEt
N N
OAc
Ph3x
O
COOEt
COOEt
N N
OAc
Ph3x
S41
O
COOEt
COOEt
N N
OAc
Ph
S
3y
O
COOEt
COOEt
N N
OAc
Ph
S
3y
S42
O
COOEt
COOEt
N N
OAc
Cl3z
O
COOEt
COOEt
N N
OAc
Cl3z
S43
O
COOEt
COOEt
N N
OAc
Cl3zz
O
COOEt
COOEt
N N
OAc
Cl3zz
S44
O
COOEt
COPh
N N
OAc
Ph5a
O
COOEt
COPh
N N
OAc
Ph5a
S45
O
COOEt
COOEt
N N
OAc
Ph3a
O
COOEt
COOEt
N N
OAc
Ph3a
S46
O
COOEt
COOEt
N N
OAc
Ph
Cl
3b
O
COOEt
COOEt
N N
OAc
Ph
Cl
3b
S47
O
COOEt
COOEt
N N
OAc
Ph3c
Br
O
COOEt
COOEt
N N
OAc
Ph3c
Br
S48
O
COOEt
COOEt
N N
OAc
Ph
F
3d
O
COOEt
COOEt
N N
OAc
Ph
F
3d
S49
O
COOEt
COOEt
N N
OAc
Ph
Br
3e
O
COOEt
COOEt
N N
OAc
Ph
Br
3e
S50
O
COOEt
COOEt
N N
OAc
Ph
Cl
3f
Br
O
COOEt
COOEt
N N
OAc
Ph
Cl
3f
Br
S51
O
COOEt
COOEt
N N
OAc
Ph
OMe
3g
O
COOEt
COOEt
N N
OAc
Ph
OMe
3g
S52
O
COOEt
COOEt
N N
OAc
Ph
MeO
3h
O
COOEt
COOEt
N N
OAc
Ph
MeO
3h
S53
O
COOEt
COOEt
N N
OAc
Ph3i
MeO
O
COOEt
COOEt
N N
OAc
Ph3i
MeO
S54
O
COOEt
COOEt
N N
OAc
Ph
Me
3j
O
COOEt
COOEt
N N
OAc
Ph
Me
3j
S55
O
COOEt
COOEt
N N
OAc
Ph
O2N
3k
O
COOEt
COOEt
N N
OAc
Ph
O2N
3k
S56
O
COOEt
COOEt
N N
OAc
Ph3l
O
COOEt
COOEt
N N
OAc
Ph3l
S57
O
COOEt
COOEt
N N
OAc
Ph
S
3m
O
COOEt
COOEt
N N
OAc
Ph
S
3m
S58
O
COOEt
COOEt
N N
OAc
Ph
F3C3n
O
COOEt
COOEt
N N
OAc
Ph
F3C3n
S59
O
COOEt
COOEt
N N
OAc
Ph3o
O
COOEt
COOEt
N N
OAc
Ph3o
S60
O
COOEt
COOEt
N N
OAc
Ph
Ph
3p
O
COOEt
COOEt
N N
OAc
Ph
Ph
3p
S61
O
COOEt
COOEt
N N
OAc
Ph
PhMeO
3q
O
COOEt
COOEt
N N
OAc
Ph
PhMeO
3q
S62
O
COOEt
COOEt
N N
OAc
Ph
Ph
MeO
3r
O
COOEt
COOEt
N N
OAc
Ph
Ph
MeO
3r
S63
O
COOEt
COOEt
N N
OAc
Ph
F3CMeO
3s
O
COOEt
COOEt
N N
OAc
Ph
F3CMeO
3s
S64
O
COOEt
COOEt
N N
OAc
Ph
F3CS
3t
O
COOEt
COOEt
N N
OAc
Ph
F3CS
3t
S65
O
COOEt
COOEt
N N
OAc
Ph3u
MeO
O
COOEt
COOEt
N N
OAc
Ph3u
MeO
S66
O
COOEt
COOEt
N N
OAc
Ph
F
3v
O
COOEt
COOEt
N N
OAc
Ph
F
3v
S67
O
COOEt
COOEt
N N
OAc
Ph3w
MeO
O
COOEt
COOEt
N N
OAc
Ph3w
MeO
S68
O
COOEt
COOEt
N N
OAc
Ph3x
O
COOEt
COOEt
N N
OAc
Ph3x
S69
O
COOEt
COOEt
N N
OAc
Ph
S
3y
O
COOEt
COOEt
N N
OAc
Ph
S
3y
S70
O
COOEt
COOEt
N N
OAc
3zCl
O
COOEt
COOEt
N N
OAc
3zCl
S71
O
COOEt
COOEt
N N
OAc
Cl
3zz
O
COOEt
COOEt
N N
OAc
Cl
3zz
S72
O
COOEt
COPh
N N
OAc
Ph5a
O
COOEt
COPh
N N
OAc
Ph5a
