1 - Memorial University of Newfoundland

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C(4) C(5) C(6) 121.5(2) C(7) C(6) C(5) 119.2(3) C(6) C(7) C(8) 120.3(3) C(7) C(8) C(9) 120.0(4) 0(3) C(9) C(4) 123.7(3) 0(3) C(9) C(8) 115.6(3) C(4) C(9) C(8) 120.8(3) 0(3) C(IO) C(11) 112.3(3) C(IO) C(11) C(3) 108.3(3) C(10) C(11) C(12) 112.4(3) C(3) C(11) C(12) 111.3(3) C(13) C(12) C(20) 113.3(3) C(13) C(12) C(11) 111.0(3) C(20) C(12) C(11) 108.6(3) C(2) C(13) C(14) 118.1(3) C(2) C(13) C(12) 120.3(3) C(14) C(13) C(12) 121.6(3) C(19) C(14) C(15) 115.6(3) C(19) C(14) C(13) 119.3(3) C(15) C(14 C(13 125.0(3) C(16) C(15) C(14) 121.7(3) C(15) C(16) C(17) 120.6(3) 305
(18) (17) (16) 120.4(3) (17) (18) (19) 117.6(3) C(18) (19) (14) 124.1(3) (18) (19) 0(1) 115.0(3) (14) q[9) 0(1) 121.0(3) (21) (20) (25) 119.0(3) (21) (20) (12) 120.4(3) (25) (20) C(12) 120.5(3) (22) (21) C(20) 121.3(3) (23) (22) (21) 117.9(3) (22) (23) (24) 123.2(3) (22) (23) N(2) 118.0(4) (24) (23) N(2) 118.8(4) (23) (24) (25) 117.7(4) (20) (25) (24) 120.9(3) 306
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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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(48) in the intramolecular Povarov
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SCHEME 3.18 Povarov Reaction betwee
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3.4 Experimental 3.4.1 General Meth
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1432 (m), 1339 (s), 1177 (w), 1026
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(C-6), 128.6 (C-n. 127.3 (C-6'), 12
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(w), 1426 (w), 1343 (m), 1319 (w),
Page 280: CH) ppm: Oc(CD,CI,) = 159.5 (C-6).
Page 287 and 288: 3.5 References I. (a) Nicolaou. K.
Page 289 and 290: S. E.: Socnen, D. R.; Miller, M. M.
Page 291: 3.6 Appendix 3.6.1 I H and lJC NMR
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Page 300 and 301: 277
Page 302 and 303: 279
Page 306: "0 283
Page 311: 1'0 288
Page 314: "0 oJ:' .J,) 291
Page 317: I II 1,1111111 II o 294
Page 321 and 322: Creagh and Hubbeli lO. All calculat
Page 324 and 325: Detector Goniometer Radiation Detec
Page 326 and 327: TABLE 3.4 Bond lengths ( ) atom ato
Page 330: 4.1 Inlroduction Chapter 4. Toward
Page 343 and 344: 4.4 Experimental 4.4.1 General Meth
Page 348 and 349: 3.94 (s, 3H) 3.57 (s. 3H), 3.39 (br
Page 350 and 351: 4.5 References 1. (a) Anthony, J. E
Page 352 and 353: 14. The synthesis of tetramethoxyet
Page 357 and 358: 334
Page 359: naming such molecules, a simpler sy
Page 365: which was accomplished previously b
Page 371: Entry TABLE 5.1 Attempted Synthesis
Page 375 and 376: SCHEME 5.14 Attempted Synthesis of
Page 377 and 378: 5.5 Experimental 5.5.1 General Meth
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was stirred at-78 "C for another 2
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7-tert-Butyl-I-(mcthoxyrnethoxy)p)'
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diethyl ether (2 x 5 mL). The combi
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solution of 34 (0.54 g, 0.92 mmol)
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(d. C-4). 125.4 (d. C-IO), 124.2 (d
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1·(1-«2·(Bu t-3·ynyl)naphthalen
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5. (a) Misek. J.; Teply, F.; Stara,
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5.7. Appendix NMR Spectra for Selec
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384
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388
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403
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