SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 2, 2007, Pages 263-267

Synthesis of optically active substituted 3-fluoropiperidines from prolinols by using DAST

(3) Déchamps, Ingrid a Pardo, Domingo Gomez a Cossy, Janine a

a CNRS (France)

Author keywords

Aziridinium; Fluorine; Piperidine; Rearrangements; Ring expansion

Indexed keywords

3 FLUOROPIPERIDINE DERIVATIVE; AZIRIDINE; FLUORIDE; N,N DIETHYLAMINOSULFUR TRIFLUORIDE; PIPERIDINE DERIVATIVE; PROLINOL DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS;

EID: 33847043960 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-967989 Document Type: Article

Times cited : (36)

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48
- 33847057274
- Compound 12: [α]D20-6.7 (c 0.135, CHCl3, IR (neat, 2921, 1460, 1252, 1153, 1090, 835, 776, 739, 699 cm-1. 1H NMR (400 MHz, CDCl3, δ, 7.40-7.15 (m, 5 H, 4.80 (dm, J, 47.2 Hz, 1 H, 4.06 (dddd, J, 9.5, 9.5, 4.5, 4.5 Hz, 1 H, 3.64 (d, J, 13.4 Hz, 1 H, 3.52 (d, J, 13.4 Hz, 1 H, 2.92-2.79 (m, 2 H, 2.29-1.99 (m, 3 H, 1.59-1.36 (m, 1 H, 0.83 (s, 9 H, 0,03 (s, 3 H, 0,01 (s, 3 H, 13C NMR: δ, 137.5 (s, 129.0 (d, 128.3 (d, 127.1 (d, 87.9 (dd, 1J C-F, 171.2 Hz, 65.1 (d, 62.3 (t, 60.2 (t, 56.0 (dt, 2JC-F, 20.2 Hz, 38.8 (dt, 2JC-F, 20.2 Hz, 25.8 (q, 18.1 (s, 4.8 (q, MS (EI, m/z (relative intensity, 323 (2, M, 308 (3, 303 (2, 290 (2, 266 (31, 246 (4, 232 (2, 192 (3, 191 (4, 190 (3, 134 (11, 102 (2, 100 2, 92
- +: 324.2159; found: 324.2151.

49
- 33847074140
- Compound 14: [α]D20 +37.6 (c 0.35, CHCl3, IR (neat, 3069, 2930, 2856, 2800, 1588, 1471, 1427, 1360, 1154, 1105, 1027, 976, 821, 738, 698 cm-1. 1H NMR (400 MHz, CDCl3, δ, 7.65-7.58 (4 H, 7.43-7.21 (11 H, 4.83 (ddddd, J, 47.7, 5.0, 5.0, 2.5, 2.5 Hz, 1 H, 4.13 (dddd, J, 8.0, 8.0, 4.0, 4.0 Hz, 1 H, 3.50 (s, 2 H, 2.74-2.58 (m, 2 H, 2.40 (ddd, J, 29.1, 12.1, 2.0 Hz, 1 H, 2.15 (m, 1 H, 1.98 (m, 1 H, 1.67 (m, 1 H, 1.04 (s, 9 H, 13C NMR (100 MHz, CDCl3, δ, 137.6 (s, 135.7 (d, 134.2 (s, 134.0 (s, 129.7 (d, 129.6 (d, 129.0 (d, 128.2 (d, 127.7 (d, 127.6 (d, 127.1 (d, 87.7 (dd, J, 170 Hz, 66.2 (dd, J, 3 Hz, 62.2 (t, 59.6 (t, 56.3 (dt, J, 21 Hz, 38.5 (dt, J, 20 Hz, 27.0 (q, 19.2 (s, MS (EI, m/z (relative intensity, 447 (1, M, 414 (2, 392 (7, 391 (27, 390 82, 370
- +: 448.2472; found: 448.2473.

50
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51
- 33847008261
- Compound 28: [α]D20 +6.6 (c 0.35, CHCl3, IR (neat, 2930, 2856, 2786, 1460, 1427, 1384, 1252, 1180, 1106, 1083, 1048, 936, 888, 821, 776, 739, 700 cm-1. 1H NMR (400 MHz, CDCl3, δ, 7.67-7.63 (m, 4 H, 7.42-7.33 (m, 6 H, 4.12 (dddd, J, 10.1, 10.1, 5.0, 5.1 Hz, 1 H, 2.90-2.83 (m, 1 H, 2.79-2.73 (m, 1 H, 2.22 (s, 3 H, 2.11-2.03 (m, 1 H, 2.00-1.78 (m, 2 H, 1.63-1.51 (m, 3 H, 1.06 (s, 9 H, 0.89 (t, J, 7.5 Hz, 3 H, 13C NMR: δ, 135.7 (d, 134.1 (s, 129.7 (d, 127.6 (d, 95.1 (ds, 1JC-F, 172 Hz, 66.4 (d, 62.3 (t, 61.7 (dt, 2JC-F, 21.2 Hz, 45.8 (q, 41.4 (dt, 2JC-F, 22.0 Hz, 31.4 (dt, 2JC-F, 22.7 Hz, 27.0 (q, 19.2 (s, 7.10 (q, MS (EI, m/z (relative intensity, 399 (2, M, 379 (12, 364 (9, 343 (28, 342 100
- +], 379 (12), 364 (9), 343 (28), 342 (100), 322 (15), 225 (7), 201 (11), 199 (13), 183 (18), 181 (10), 144 (18), 124 (30), 122 (23), 94 (11), 58 (12).

52
- 33847074573
- The ee values were determined by HPLC: OJ-H, hexane, 0.3 mL/min
- The ee values were determined by HPLC: OJ-H, hexane, 0.3 mL/min.

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- Benzyl and allyl neighboring groups are reported to participate in DAST reactions in the absence of internal nucleophile, for examples, see: (a) Haigh, D.; Jefcott, L. J.; Magge, K.; McNab, H. J. Chem. Soc., Perkin Trans. 1 1996, 1895.

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