Stereoselective 1,3-Dipolar Cycloaddition of a Maleate Derivative with Azomethine Ylides Derived from α-Amino Esters: Synthesis of 3-Pyrrolines

Adrien Soret; Régis Guillot; Gérard Rousseau; Luis Blanco; Sandrine Deloisy

doi:10.1055/s-2007-977449

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Synlett 2007(8): 1284-1288
DOI: 10.1055/s-2007-977449

LETTER

Stereoselective 1,3-Dipolar Cycloaddition of a Maleate Derivative with Azomethine Ylides Derived from α-Amino Esters: Synthesis of 3-Pyrrolines

Adrien Soret^a, Régis Guillot^b, Gérard Rousseau^a, Luis Blanco^a, Sandrine Deloisy*^a
^a Laboratoire de Synthèse Organique et Méthodologie, Institut de Chimie Moléculaire et des Matériaux d’Orsay (CNRS), Bât. 420, Université Paris-Sud, 91405 Orsay Cedex, France
Fax: +33(1)69156278; e-Mail: sdeloisy@icmo.u-psud.fr;
^b Service de Cristallographie, ICMMO (CNRS), Bât. 420, Université Paris-Sud, 91405 Orsay Cedex, France

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Publication History

Received 13 December 2006
Publication Date:
08 May 2007 (online)

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Abstract

A new preparation of 3-pyrrolines is described by [3+2] cycloadditions of N-metalated azomethine ylides derived from α-amino esters with a dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate derivative, followed by retro-Diels-Alder reactions. This two-step sequence appears superior to the direct reaction of ylides with dimethyl acetylenedicarboxylate and should be applicable to solid-phase synthesis.

Key words

cycloadditions - amino esters - ylides - diastereoselectivity - retro reactions

References and Notes

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7

Trimethyl (1 S *,3 S *,3a R *,4 R *,7 S *,7a S *)-7-[4-(Benzyl-oxy)phenylmethyl]-3-phenyl-2,3,3a,4,7,7a-hexahydro-1 H -4,7-epoxyisoindole-1,3a,7a-tricarboxylate (4a)
White solid; mp 106 °C. ¹H NMR (400 MHz, CDCl₃): δ = 2.93 (s, 3 H), 3.25 (d, J = 15.2 Hz, 1 H), 3.48 (d, J = 15.2 Hz, 1 H), 3.81 (s, 3 H), 3.86 (s, 3 H), 4.41 (s, 1 H), 4.45 (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, CDCl₃): 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, 1581, 1511, 1452, 1431, 1245, 1222, 1106 cm^-1. MS (ES⁺): m/z (%) = 320 (100) [pyrroline 10 + H]⁺, 342 (16) [pyrroline 10 + Na]⁺. Anal. Calcd for C₃₄H₃₃NO₈: C, 69.97; H, 5.70; N, 2.40. Found: C, 69.81; H, 5.67; N, 2.27.

8

Trimethyl (1 S *,3 S *,3a R *,4 S *,7 R *,7a S *)-1-[4-(Benzoyl-oxy)phenylmethyl]-4-[4-(benzyloxy)phenylmethyl]-3-phenyl-2,3,3a,4,7,7a-hexahydro-1 H -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), 6.49 (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, 81.7, 83.6, 96.9, 114.1, 120.9, 127.4, 127.7, 127.8, 127.9, 128.1, 128.5, 130.1, 130.4, 131.0, 131.6, 131.8, 132.5, 133.2, 133.3, 133.4, 137.1, 137.4, 145.6, 149.6, 157.1, 165.0, 169.5, 170.6, 172.9. IR (neat): 3327, 3060, 3028, 3005, 2951, 2851, 1738, 1729, 1713, 1604, 1584, 1506, 1469, 1451, 1433, 1245, 1198, 1169, 1080, 1060 cm^-1. MS (ES⁺): m/z (%) = 522 (100) [pyrroline 9f + Na]⁺.

9

Trimethyl (1 S *,3 S *,3a R *,4 S *,7 R *,7a S *)-4-[4-(Benzyl-oxy)phenylmethyl]-1-methyl-3-phenyl-2,3,3a,4,7,7a-hexahydro-1 H -4,7-epoxyisoindole-1,3a,7a-tri-carboxy-late (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, 3 H), 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, 3062, 3032, 3003, 2951, 1744, 1726, 1654, 1611, 1511, 1454, 1434, 1249, 1225, 1079 cm^-1. MS (ES⁺): m/z (%) = 274 (33), 334 (100), 598 (15) [M + H]⁺. HRMS (ES⁺): m/z calcd for C₃₅H₃₆O₈N: 598.2435; found: 598.2453.

10

Trimethyl (2 S *,5 S *)-2-Methyl-5-phenyl-2,5-dihydro-1 H -pyrrole-2,3,4-tricarboxylate (9b) White solid; mp 62-63 °C. ¹H NMR (400 MHz, CDCl₃): 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.

11

Trimethyl (2 S *,5 S *)-2-[4-(Benzoyloxy)phenylmethyl]-5-phenyl-2,5-dihydro-1 H -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, CDCl₃): 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 C₃₀H₂₇O₈NNa: 552.1629; found: 552.1628.

12

Trimethyl (3 S *,4 S *,5 R *)-5-Phenyl-4,5-dihydro-3 H -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 C₁₆H₁₇O₆NNa: 342.0948; found: 342.0955.

14

Trimethyl (2 S *,5 S *)-1-(Phenylcarbamoyl)-5-phenyl-2,5-dihydro-1 H -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), 7.41-7.48 (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 C₂₃H₂₂O₇N₂Na: 461.1319; found: 461.1328.

15

X-ray Crystal Data of 9b C₁₇H₁₉NO₆, 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.

17

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

18

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