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INVERSE ELECTRON DEMAND DIELS-ALDER
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Abstract The Dicls-Alder reaction i
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Acknowledgements I am thankful 10 m
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1.4.2.1 Representative Procedure A:
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3.2.3 Scope of Inrramolecular Povar
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List of Tables TABLE 1.1 Optimizati
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list of Figures FIGURE 1.1 3tural A
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SCHEME 3.4 Talal Synthesis of rac-y
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List or Abbreviations Ab, APeI calc
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1.2.3 Synlhesis of Various 3-Aminoc
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1.4.2.4 Representative Procedure D:
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(7-Hydroxy-2.oxo.2JJ-chromen.3-yl)c
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According 10 representalive procedu
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128.5, 126.5, 125.8, 122.2, 119.0,
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----------------------------- 3-«2
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According to representative procedu
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3. (a) Nine!, L.; Benazel, F.; Char
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m "" NHAc "" "" I A 0 0 51 53
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Me'CC::(NHBoc a a 50 56
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1\ 71
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1 73
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aldehyde. was investigated. Indeed.
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the ground state to the transition
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perfonned in the presence of a pote
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any further beneficial effect on th
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(F;g.2.2). 51 FIGURE 2.2 A possible
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2.4.2 General EXI)Crimental Procedu
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1.57-1.51 (m. 1H). 1.47-1.42 (m. 2H
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acetatelhexanes) to afford 26a as a
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(m. IH. H-2). 3.40-3.35 (m, IH. H-3
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2.46 (s. 3H. COCH,), 2.38-2.33 (m.
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------------, 2.31 (s. 3H, OCOCHJ)
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1.80-1.76 (m, IH, H-3) ppm; liC
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COOCH,), 3.97-3.92 (m, IH, H-2). 3.
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Hz, IH, H-8), 5.40 (d, j =6.1 Hz, I
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(m). 1020 (w) em']; MS (APCI) m/: (
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(4aS·, 5R·, 12cS·)-4-(7-Oxo·2,3
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(30-100% ethyl acet'l.Ielhexanes) t
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Acetic acid-4-[3-(2-hydroxyethyl)-1
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3 min. After the addition, the reac
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2.5 References I. For review articl
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62. 3977-3984. 12. Povarov, L. S. C
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see: Anderson, H. J.; Loader. C E.;
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2.6 Appendix 2.6.1 I H and IJC NMR
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160
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164
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"0 167
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170
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"0 I I III II I I I I I I 150 100 5
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COOCI"J 176
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181
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." 188
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The data were collected at a temper
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The standard deviation of an observ
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Detector Goniometer Radiation Detec
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C. Structure Solution and Refinemen
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C(24) C(25) 1.370(3) C(26) C(27) 1.
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C(8) C(7) C(IO) 119.5(2) N(I) C(8)
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C(30) C(31) C(32) 123.9(2) C(31) C(
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Chapter 3. Intramolecular Inverse E
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- Page 254 and 255: SCHEME 3.18 Povarov Reaction betwee
- Page 256 and 257: 3.4 Experimental 3.4.1 General Meth
- Page 260: 1432 (m), 1339 (s), 1177 (w), 1026
- Page 268 and 269: (C-6), 128.6 (C-n. 127.3 (C-6'), 12
- Page 272 and 273: (w), 1426 (w), 1343 (m), 1319 (w),
- Page 280: CH) ppm: Oc(CD,CI,) = 159.5 (C-6).
- Page 288 and 289: Cram, D. J.; Knox, G. R. J. Am. Che
- Page 290 and 291: 7133. 17. Cao. X.; Yang, Y.; Wang,
- Page 293 and 294: 270
- Page 295: o,..r\:O (X:(H A 0 0 .. .. ,,. ....
- Page 301 and 302: 278
- Page 303: I, I I I w,e I 280
- Page 309: "0 286
- Page 313 and 314: 290
- Page 316 and 317: 293
- Page 319: (0 scans from -75.0 to 105.00 in 0.
- Page 322: (8) lbers, J. A. & Hamilton. W. c.;
- Page 325 and 326: Structure Solution Refinement Funct
- Page 327 and 328: TABLE 3.5 Bond angles (0) atom atom
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the dienophile were used. Although
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4.4.2 S)'nthcsis and Characterizati
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7.0 Hz. 3H. H-IO') ppm; Oc(CDCI,) =
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7. Dang, A.-T.; Miller, D.O.; Dawe,
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4.6 Appendix 8, 40 OM. CaOMe 330
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Chapter 5. Toward the Synthesis of
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Hclicenes having wider aromatic bac
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with trimethylsilylacctylene (TMSA)
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Ihat of propargylmagnesiumbromide d
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5.4 Conclusion Although the synthes
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system and high-resolution mass spe
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41. 1.57 (s. 9H. H-2") ppm, Oc(CDCI
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1.57 (s. 9H. H-2"') ppm; lic(CDClJ)
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Hz. 1H). 7.90 (d. J =9.2 Hz. 1H). 7
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(7-lert-Butyl-I-«trimcthylsilyl)ct
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I-(7-/ert-But)'1·1-((2-(4·triisop
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4",).5.06 (ddl. J = 10.2, 1.8. 1.1
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20. Hofsl0kken. N. U.; Skattebpl. L
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.. 32 382
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386
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394