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Volumn , Issue 8, 2007, Pages 1284-1288

Stereoselective 1,3-dipolar cycloaddition of a maleate derivative with azomethine ylides derived from α-amino esters: Synthesis of 3-pyrrolines

(5) Soret, Adrien a Guillot, Régis a Rousseau, Gérard a Blanco, Luis a Deloisy, Sandrine a

a UNIVERSITÉ PARIS SUD (France)

Author keywords

Amino esters; Cycloadditions; Diastereoselectivity; Retro reactions; Ylides

Indexed keywords

3 PYRROLINE DERIVATIVE; ALPHA AMINO ESTER DERIVATIVE; AZOMETHINE YLIDE; DIMETHYL 7 OXABICYCLO[2.2.1]HEPTA 2,5 DIENE 2,3 DICARBOXYLATE DERIVATIVE; ESTER DERIVATIVE; MALEIC ACID DERIVATIVE; PYRROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; SYNTHESIS;

EID: 34249798194 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-977449 Document Type: Article

Times cited : (7)

References (26)

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6
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- (2002) The Chemistry of Heterocyclic Compounds , vol.59 , pp. 169-252
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- Broggini, G.¹ Zecchi, G.²

12
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13
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14
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15
- 85083867562
- Trimethyl (1S*,3S*, 3aR*,4R*,7S*, 7aS*)-7-[4-(Benzyloxy)phenylmethyl]-3-phenyl-2,3,3a,4,7, 7a-hexahydro-1H-4,7-epoxyisoindole-1,3a,7a-tricarboxylate (4a) White solid; mp 106°C. 1H NMR (400 MHz, CDCl 3, δ, 2.93 (s, 3 H, 3.25 (d, J, 15.2 Hz, 1 H, 348 (d, J, 15.2 Hz, 1 H, 3.81 (s, 3 H, 3.86 (s, 3 H, 4.41 (s, 1 H, 445 (s, 1 H, 4.95 (s, 1 H, 5.07 (s, 2 H, 6.15 (d, J, 6.0 Hz. 1 H, 6.66 (d, J, 6.0 Hz, 1 H, 6.96 (d, J, 8.4 Hz, 2 H, 7.27 (d, J, 8.4 Hz, 2 H, 7.29-7.92 (m, 10 H, 13C NMR (100 MHz, CDCl 3, δ, 35.0, 51.5, 52.0, 52.4, 66.6, 70.0. 70.1, 73.5, 82.6, 83.9, 94.5, 114.5, 127.2, 127.6, 128.1, 128.4, 128.5, 128.6, 129.3, 131.4, 133.4, 137.2, 137.8, 141.3, 157.6, 169.8, 170.9, 171.2. IR KBr, 3307, 1744, 1731, 1609
- 8: C, 69.97; H, 5.70; N, 2.40. Found: C, 69.81; H, 5.67; N, 2.27.

16
- 85083868412
- Trimethyl (1S*,3S*, 3aR*,4S*,7R*, 7aS*)-1-[4-(Benzoyloxy)phenylmethyl]-4-[4-(benzyloxy) phenylmethyl]-3-phenyl-2,3,3a,4,7,7a-hexahydro-1H-4, 7-epoxyisoindole-1,3a,7a-tricarboxylate (7f) Oil. 1H NMR (250 MHz, CDCl3, δ, 1.95 (d, J, 15.0 Hz, 1 H, 2.40 (d, J, 15.0 Hz, 1 H, 3.09 (d, J, 14.0 Hz, 1 H, 3.49 (d, J, 14.0 Hz, 1 H, 3.73 (s, 3 H, 3.84 (s, 3 H, 3.99 (s, 3 H, 4.77 (d, J, 1.8 Hz, 1 H, 4.94 (s, 2 H, 5.97 (br s, 1 H, 6.00 (dd, J, 5.5, 1.8 Hz, 1 H, 649 (d, J, 5.5 Hz, 1 H, 6.75 (d, J, 8.8 Hz, 2 H, 6.90 (d, J, 8.8 Hz, 2 H, 7.04 (d, J, 8.5 Hz, 2 H, 7.31-7.60 (m, 15 H, 8.15 (d, J, 7.0 Hz, 2 H, 13C NMR 62.9 MHz, CDCl3, δ, 35.1, 37.1, 52.1, 52.5, 52.8, 65.2, 69.8, 70.8, 74.4, 81
- +.

17
- 85083867987
- Trimethyl (1S*,3S*, 3aR*,4S*,7R*, 7aS*)-4-[4-(Benzyloxy)phenylmethyl]-1-methyl-3-phenyl-2,3, 3a,4,7,7a-hexahydro-1H-4,7-epoxyisoindole-1,3a, 7a-tri-carboxylate (7b) Oil. 1H NMR (400 MHz, CDCl3, δ, 1.62 (s, 3 H, 1.96 (d, J, 14.8 Hz, 1 H, 2.37 (d, J, 14.8 Hz, 1 H, 3.63 (s, 3 H, 3.91 (s, 3H, 3.94 (s, 3 H, 4.21 (br s, 1 H, 4.84 (br s, 1 H, 4.94 (s, 2 H, 5.71 (s, 1 H, 5.94 (d, J, 5.2 Hz, 1 H, 6.45 (d, J, 5.2 Hz, 1 H, 6.74 (d, J, 8.8 Hz, 2 H, 6.89 (d, J, 8.8 Hz, 2 H, 7.24-7.60 (m, 10 H, 13C NMR (100 MHz, CDCl3, δ, 21.3, 34.9, 51.7, 52.4, 52.6, 65.7, 69.2, 69.7, 69.9, 80.9, 83.0, 96.7, 113.9, 127.2, 127.6, 127.7, 128.2, 128.3, 130.3, 130.4, 130.8, 132.0, 136.9, 137.3, 145.4, 156.9, 169.3, 171.7, 171.9. IR neat, 3450
- 8N: 598.2435; found: 598.2453.

18
- 85083869365
- Trimethyl (2S*,5S*)-2- Methyl-5-phenyl-2,5-dihydro-1H-pyrrole-2,3,4-tricarboxylate (9b) White solid; mp 62-63°C. 1H NMR (400 MHz, CDCl 3, δ, 1.66 (s, 3 H, 2.74 (br s, 1 H, 3.60 (s, 3 H, 3.80 (s, 3 H, 3.83 (s, 3 H, 5.35 (s, 1 H, 7.20-7.35 (m, 5 H, 13C NMR (100 MHz, CDCl3, δ, 24.8, 52.2, 52.4, 52.9, 69.0, 73.0, 127.4, 128.3, 128.4, 140.1, 140.9, 141.2, 163.5, 163.7, 172.9. IR (KBr, 3359, 2992, 2950, 2832, 1733, 1715, 1656, 1449, 1433, 1334, 1244, 1204 cm -1. MS (ES, m/z, 274 (74, 334 (77, M, H, 356 (100, M, Na, HRMS ES, m/z calcd for C17H19O6NNa: 356.1105; found: 356.1119
- 6NNa: 356.1105; found: 356.1119.

19
- 85083867802
- Trimethyl (2S*,5S*)-2-[4, Benzoyloxy)phenylmethyl]-5-phenyl-2,5-dihydro-1H-pyrrole-2,3, 4-tricarboxylate (9f) Oil. 1H NMR (250 MHz, CDCl3, δ, 2.83 (br s, 1 H, 3.32 (s, 2 H, 3.54 (s, 3 H, 3.80 (s, 3 H, 3.90 (s, 3 H, 4.68 (br s, 1 H, 7.14 (d, J, 8.5 Hz, 2 H, 7.26-7.30 (m, 5 H, 7.42 (d, J, 8.5 Hz, 2 H, 7.46-7.52 (m, 2 H, 7.57-7.67 (m, 1 H, 8.20 (d, J, 7.0 Hz, 2 H, 13C NMR (62.9 MHz, CDCl 3, δ, 42.5, 52.0, 52.5, 52.8, 69.1, 77.5, 121.1, 127.7, 128.1, 128.5, 128.6, 129.5, 130.0, 131.8, 133.1, 133.5, 140.4, 140.7, 141.1, 150.0, 162.7, 164.5, 165.0, 171.9. IR (neat, 3367, 3063, 3032, 3005, 2953, 2847, 1739, 1731, 1713, 1659, 1601, 1507, 1452, 1434, 1250, 1200, 1168, 1082, 1063, 1024 cm-1. MS (ES, m/z, 552 (100, M, Na, HRMS ES, m/z calcd for C 30H
- 8NNa: 552.1629; found: 552.1628.

20
- 85083869351
- Trimethyl (3S*,4S*, 5R*)-5-Phenyl-4,5-dihydro-3H-pyrrole-2,3, 4-tricarboxylate (10) Oil. 1H NMR (400 MHz, CDCl3, δ, 3.15 (s, 3 H, 3.76 (s, 3 H, 3.87 (dd, J, 9.2, 6.0 Hz, 1 H, 3.93 (s, 3 H, 4.72 (dd, J, 6.0, 2.4 Hz, 1 H, 5.86 (dd, J, 9.2, 2.4 Hz, 1 H, 7.05-7.08 (m, 2 H, 7.22-7.32 (m, 3 H, 13C NMR (100 MHz, CDCl3, δ, 51.8. 52.7, 52.9, 56.5, 56.6, 78.9, 127.4, 128.2, 128.3, 135.6, 161.9, 164.0, 170.0, 170.1. IR (neat, 3059, 3033, 3007, 2956, 2919, 2847, 1726, 1648, 1452, 1437, 1369, 1312, 1258, 1217, 1101 cm -1. MS (ES, m/z, 260 (100, 342 (82, M, Na, HRMS ES, m/z calcd for C 16H17O6NNa: 342.0948; found: 342.0955
- 6NNa: 342.0948; found: 342.0955.

21
- 0025830860
- Katritzky, A. R.; Hitchings, G. J.; Zhao, X. Synthesis 1991, 863.
- (1991) Synthesis , pp. 863
- Katritzky, A.R.¹ Hitchings, G.J.² Zhao, X.³

22
- 85083869179
- Trimethyl (2S*,5S*)-1, Phenylcarbamoyl)-5-phenyl-2,5-dihydro-1H-pyrrole-2,3, 4-tricarboxylate (11) White solid; mp 156-157°C. 1H NMR (250 MHz, CDCl3, δ, 3.69 (s, 3 H, 3.86 (s, 3 H, 3.93 (s, 3 H, 5.60 (d, J, 3.0 Hz, 1 H, 5.96 (d, J, 3.0 Hz, 1 H, 6.76 (br s, 1 H, 6.99 (t, J, 8.6 Hz, 1 H, 7.14 (d, J =7.6 Hz, 2 H, 7.19-7.22 (m, 2 H, 741-748 (m, 3 H, 7.72 (d, J, 7.2 Hz, 2 H, 13C NMR (62.9 MHz, CDCl3, δ, 52.3, 52.6, 52.9, 67.0, 69.3, 119.2, 123.2, 127.9, 128.6, 129.1, 129.2, 131.2, 136.5, 137.8, 140.6, 152.9, 161.8, 161.9, 169.5. IR (neat, 3365, 3033, 3007, 2956, 2919, 2847, 1749, 1726, 1646, 1541, 1447, 1434, 1363, 1333, 1279, 1247 cm -1. MS (ES, m/z, 461 (100, M, Na, HRMS ES, m/z calcd for C23H 22O7N2
- 2Na: 461.13 19; found: 461.1328.

23
- 85083870111
- X-ray Crystal Data of 9b C17H19NO 6, M, 333.33, triclinic, space group P-1, Z, 2, a, 6.0095 (8) Å, b, 8.1268 (13) Å, c, 18.151 (3) Å, α, 78.363 (3)°, β, 89.035 (2)°, γ, 77.285 (3)°, V, 846.6 (2) Å3, d, 1.308 g/cm3, 3217 independent reflections were collected with MoKα radiation on Kappa X8 APEX II system. Data analysis was carried out with Bruker program SMART and SAINT,17 the structure was solved and refined by direct methods using SHELXTL program18 to R1, 0.0572, wR2, 0.1505. The supplementary crystallographic data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.uk/data_request/cif. Please quote reference number CDDC 630085
- 18 to R1 = 0.0572, wR2 = 0.1505. The supplementary crystallographic data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.uk/data_request/cif. Please quote reference number CDDC 630085.

24
- 33646767009
- Farrugia, L. J. J. Appl. Cryst. 1997, 30, 565.
- (1997) J. Appl. Cryst , vol.30 , pp. 565
- Farrugia, L.J.¹

25
- 85083866471
- Bruker SMART and SAINT, Bruker AXS Inc., Madison, Wisconsin, USA, 1997.
- Bruker SMART and SAINT, Bruker AXS Inc., Madison, Wisconsin, USA, 1997.

26
- 85083867588
- Bruker SHELXTL, Version 6.3.1, Bruker AXS Inc, Madison, Wisconsin, USA, 2004
- Bruker SHELXTL, Version 6.3.1, Bruker AXS Inc., Madison, Wisconsin, USA, 2004.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.