Ph.D. Thesis_AS_Publishing version for IRC_12 ... - Jacobs University

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3.3.2 Catalyst system investigations ................................................................................... 64 3.4 Asymmetric Michael addition of α-substituted aldehydes to maleimides ................ 66 3.5 DFT supported mechanism ........................................................................................ 73 3.6 Absolute and relative stereochemistry ....................................................................... 83 3.7 Conclusion ................................................................................................................. 99 References .............................................................................................................................. 100 Chapter 4. Experimental: Diamine catalysts ..................................................................... 103 4.1 General information ................................................................................................. 104 4.2 Procedure for the synthesis of diamine catalysts ..................................................... 104 4.3 Racemate formation ................................................................................................. 101 4.3.1 General procedure for synthesis of racemic Michael adducts (ketones) ................. 106 4.3.2 General procedure for synthesis of racemic Michael adducts (aldehydes) ............. 106 4.4 General procedure for enantioselective reactions .................................................... 106 4.5 Analytical data (text) ............................................................................................... 107 References .............................................................................................................................. 112 Chapter 5. Experimental: Assembled bifunctional catalysts section .............................. 113 5.1 General information ................................................................................................. 114 5.2 Racemate formation ................................................................................................. 116 5.3 General procedure for enantioselective reactions .................................................... 116 5.4 Analytical data (text) ............................................................................................... 117 References .............................................................................................................................. 127 IX
Chapter 6. Spectra (HPLCs and NMRs) ............................................................................ 128 Publication references with abstracts ................................................................................. 185 X
Page 1 and 2: Bifunctional Organocatalysts Contai
Page 3 and 4: Acknowledgements I would like to co
Page 5 and 6: EtOAc GC h HPLC HRMS Hz IR J m M Me
Page 7 and 8: Abstract The asymmetric Michael add
Page 9: 1.5 Research goals: bifunctional ba
Page 13 and 14: Chapter 1 1.1 Organocatalysis In pa
Page 15 and 16: Chapter 1 • Easy and promising pr
Page 17 and 18: Chapter 1 Scheme 1.5 shows a possib
Page 19 and 20: Chapter 1 O O O N R (S)-proline DMS
Page 21 and 22: Chapter 1 1.4 Asymmetric Michael ad
Page 23 and 24: Chapter 1 O R Michael product R' Ar
Page 25 and 26: Chapter 1 bifunctional catalysts st
Page 27 and 28: Chapter 1 proposed that the seconda
Page 29 and 30: Chapter 1 Ph NH 2 Ph N H S N H NH N
Page 31 and 32: Chapter 1 Amino-sulfoneamides N H 2
Page 33 and 34: Chapter 1 acetone with only 16% ee.
Page 35 and 36: Chapter 1 X X NH 2 COOK NH N Cl 46
Page 37 and 38: Chapter 1 O O O O O O S O 50 51 52
Page 39 and 40: Chapter 1 Summary for the asymmetri
Page 41 and 42: Chapter 1 4 25b 13 / 5 7 120 rt 63
Page 43 and 44: Chapter 1 Table 1.4: Summary for th
Page 45 and 46: Chapter 1 20 48a O H O O N Ph 15/10
Page 47 and 48: Chapter 1 References 1. Selected re
Page 49 and 50: Chapter 1 33. B. Tan, X. Zeng, Y. L
Page 51 and 52: Chapter 2 RESULTS AND DISCUSSION: D
Page 53 and 54: Chapter 2 enamine. Meanwhile, the p
Page 55 and 56: Chapter 2 2.3 Model reaction: cyclo
Page 57 and 58: Chapter 2 2.1, entry 3). THF and a
Page 59 and 60: Chapter 2 2.4 Asymmetric Michael ad
Page 61 and 62:
Chapter 2 Table 2.4: Asymmetric Mic
Page 63 and 64:
Chapter 2 Ph NH N H H N Ph NH 97 98
Page 65 and 66:
Chapter 2 A final convincing argume
Page 67 and 68:
Chapter 2 References 1. S. H. McCoo
Page 69 and 70:
Chapter 3 3.1 Introduction Asymmetr
Page 71 and 72:
Chapter 3 ineraction, as shown in S
Page 73 and 74:
Chapter 3 CF 3 CF 3 O S O O H 2 N N
Page 75 and 76:
Chapter 3 Table 3.2: Solvent screen
Page 77 and 78:
Chapter 3 4 71 99 10 O t Bu-L-threo
Page 79 and 80:
Chapter 3 Table 3.4: Asymmetric Mic
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Chapter 3 20 B H O O N Ph O 134 16
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Chapter 3 16 [b], [d] 1,2-dimethoxy
Page 85 and 86:
Chapter 3 To better appreciate the
Page 87 and 88:
Chapter 3 Ph Me O 3.20 tBuO Ph N N
Page 89 and 90:
Chapter 3 Figure 3.4. Steric based
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Chapter 3 permit fundamentally diff
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Chapter 3 These combined results de
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Chapter 3 1 H NMR (400 MHz, CDCl 3
Page 97 and 98:
Chapter 3 methyl group of the minor
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Page 101 and 102:
Chapter 3 Figure 3.13. Expansion fr
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Chapter 3 Please refer to α-ethyl
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Chapter 3 13 C NMR (100 MHz, CDCl 3
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Chapter 3 129.19, & 131.93 ppm repr
Page 111 and 112:
Chapter 3 References 1. For the reg
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Chapter 3 19. The potassium complex
Page 115 and 116:
Chapter 4 4.1 General information A
Page 117 and 118:
Chapter 4 4.3 Racemate formation 4.
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Chapter 4 O NO 2 (S)-2-((R)-2-nitro
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Chapter 4 MS (EI), m/z (relative in
Page 123 and 124:
Chapter 4 References 1. The two ena
Page 125 and 126:
Chapter 5 5.1 General information R
Page 127 and 128:
Chapter 5 5.2 Racemate formation To
Page 129 and 130:
Chapter 5 The ee was determined by
Page 131 and 132:
Chapter 5 (S)-1-(2,5-dioxo-1-phenyl
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Chapter 5 (S)-3-(benzo[d][1,3]dioxo
Page 135 and 136:
Chapter 5 (S)-2,6-dimethyl-2-((S)-2
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Page 139 and 140:
Chapter 6 SPECTRA (HPLCs AND NMRs)
Page 141 and 142:
Chapter 6 HPLC of 2,2,2-trifluoro-N
Page 143 and 144:
Chapter 6 HPLC of 2-(2-nitro-1-p-to
Page 145 and 146:
Chapter 6 HPLC of 2-(1-(furan-2-yl)
Page 147 and 148:
Chapter 6 HPLC of 2,2-dimethyl-4-ni
Page 149 and 150:
Chapter 6 HPLC of 3-(4-methoxypheny
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Chapter 6 140
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Chapter 6 142
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Chapter 6 144
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Chapter 6 146
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Chapter 6 148
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Chapter 6 150
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Chapter 6 HPLC of 2-(1-benzyl-2,5-d
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Chapter 6 HPLC of 1-(2,5-dioxo-1-ph
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Chapter 6 HPLC of 3-(benzo[d][1,3]d
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Chapter 6 HPLC of 2-methyl-2-(2,5-d
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Chapter 6 164
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Chapter 6 166
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Chapter 6 168
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Chapter 6 170
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Chapter 6 172
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Chapter 6 174
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Chapter 6 176
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Chapter 6 178
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Chapter 6 180
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Chapter 6 182
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Chapter 6 184
Page 197:
Publication # 02 Sequential Reducti
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