Efficient Synthesis of New Macrocycles with Planar Chirality

Jarosław Kalisiak; Janusz Jurczak

doi:10.1055/s-2004-829082

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Synlett 2004(9): 1616-1618
DOI: 10.1055/s-2004-829082

LETTER

Efficient Synthesis of New Macrocycles with Planar Chirality

Jarosław Kalisiak^a, Janusz Jurczak*^a,b
^a Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
^b Department of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland
Fax: +48(22)6326681; e-Mail: jurczak@icho.edu.pl;

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Publikationsverlauf

Received 24 March 2004
Publikationsdatum:
29. Juni 2004 (online)

Abstract
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Abstract

Two new macrocycles possessing planar chirality were efficiently synthesized and resolved into enantiomers employing HPLC. CD spectra of 11 and 12 confirm their enantiomeric relationship and chiral stability.

Key words

amides - macrocycles - synthesis - supramolecular chemistry - enantiomeric resolution

References

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11

General Procedure for Synthesis of Macrocyclic Compounds 10-12: To a mixture of appropriate ester (5 mmol) and appropriate amine (5 mmol) in anhyd MeOH (60 mL) was added solution of MeONa (12.5 mmol) in anhyd MeOH (50 mL). The mixture was left at r.t. for several hours (monitored by TLC). The solvent was evaporated and the residue was purified by column chromatography.

13

19-Benzyloxy-2,8,14-trioxa-5,11-diaza-bicyclo[13.3.1]nonadeca-1 (18),15 (19),16-triene-4,12-dione ( 10). Purified by column chromatography (silica gel, EtOAc) to give 10 (60%) as a white solid; mp 183.9-184.5 °C. ¹H NMR (500 MHz, DMSO-d ₆): δ = 7.82-7.76 (m, 2 H, NHCO), 7.60 (d, J = 7.0 Hz, 2 H), 7.48 (t, J = 7.0 Hz, 2 H), 7.43-7.39 (m, 1 H), 7.16 (dd, J ₁ = 1.9 Hz, J ₂ = 7.3 Hz, 1 H), 7.09 (d, J = 7.8 Hz, 2 H), 5.04 (s, 2 H, CH₂Ph), 4.76 (d_AB, J = 16.5 Hz, 2 H, CH₂CO), 4.69 (d_AB, J = 16.5 Hz, 2 H, CH₂CO), 3.52-3.43 (m, 2 H), 3.12-3.05 (m, 4 H), 2.87-2.82 (m, 2 H). ¹³C NMR (125 MHz, DMSO-d ₆): δ = 167.9, 152.7, 139.4, 136.1, 128.8, 128.7, 128.6, 128.5, 125.9, 125.7, 113.4, 113.2, 76.7, 71.3, 68.4, 38.6. HR-ESI (MeOH): m/z [M + Na]⁺ calcd for C₂₁H₂₄N₂O₆Na: 423.1532; found: 423.1542. Anal. Calcd for C₂₁H₂₄N₂O₆: C, 63.00; H, 6.00; N, 7.00. Found: C, 63.10; H, 6.01; N, 7.06.

15

19-Benzyloxy-18-bromo-2,8,14-trioxa-5,11-diaza-bicyclo[13.3.1]nonadeca-1 (18),15 (19),16-triene-4,12-dione ( 11). Purified by column chromatography (silica gel, EtOAc) to give 11 (1720 mg, 72%) as a white solid; mp 172.6-173.6 °C. ¹H NMR (500 MHz, CDCl₃): δ = 8.59-8.53 (br d, 1 H, NHCO), 7.99-7.93 (br d, 1 H, NHCO), 7.58-7.54 (m, 2 H), 7.46-7.41 (m, 3 H), 7.37 (d, J = 9 Hz, 1 H), 6.81 (d, J = 9 Hz, 1 H), 5.06 (d_AB, J = 9.5 Hz, CH₂Ph, 1 H), 4.99 (d_AB, J = 9.5, CH₂Ph, 1 H), 4.89 (d_A1B1, J = 16.5, CH₂CO, 1 H), 4.82 (d_A2B2, J = 16.1 Hz, CH₂CO, 1 H), 4.63 (d_A1B1, J = 16.5 Hz, CH₂CO, 1 H), 4.52 (d_A2B2, J = 16.1 Hz, CH₂CO), 3.80-3.71 (m, 2 H), 3.19-3.10 (m, 3 H), 3.04-2.99 (m, 1 H), 2.96-2.88 (m, 1 H), 2.64-2.57 (m, 1 H). ¹³C NMR (125 MHz, CDCl₃): δ = 168.5, 168.1, 153.0, 151.3, 142.5, 134.9, 130.2, 129.8, 129.3, 128.8, 115.5, 109.1, 78.5, 73.8, 72.5, 69.3, 69.1, 38.9, 38.8. HR-ESI (MeOH): m/z [M + Na]⁺ calcd for C₂₁H₂₃N₂O₆ ⁷⁹BrNa: 501.0632; found: 501.0646. Anal. Calcd for C₂₁H₂₃N₂O₆Br: C, 52.62; H, 4.84; N, 5.84; Br, 16.67. Found: C, 52.49; H, 4.93; N, 5.63; Br, 16.52.

17

11-Bromo-26-(1-naphthylmethoxy)-2,8,15,21-tetraoxa-5,18-diaza-tricyclo[20.3.1.0*9,14*]hexacosa-1 (25),9 (14),10,12,22 (26),23-hexaene-4,19-dione ( 12). Purified by column chromatography (silica gel, EtOAc) to give 12 (465 mg, 15%) as white solid; mp 166.5-167.8 °C. ¹H NMR (500 MHz, CDCl₃): δ = 8.30-8.26 (m, 1 H), 7.98-7.93 (m, 2 H, NHCO), 7.85-7.80 (m, 1 H), 7.74-7.67 (m, 2 H), 7.52-7.47 (m, 2 H), 7.35-7.30 (m, 1 H), 7.13 (t, 1 H, J = 8.4), 6.89 (dd, 1 H, J ₁ = 8.6 Hz, J ₂ = 2.2 Hz), 6.79-6.74 (m, 2 H), 6.55 (d, 1 H, J = 2.2 Hz), 6.36 (d, 1 H, J = 8.6 Hz), 5.47 (s, 2 H, CH₂Naph), 4.79 (dd_AB, J ₁ = 8.2 Hz, J ₂ = 15.6 Hz, 2 H, CH₂CO), 4.58 (d_AB, J = 15.6 Hz, 2 H, CH₂CO), 3.90-3.80 (m, 2 H), 3.71-3.65 (m, 1 H), 3.62-3.52 (m, 3 H), 3.38-3.30 (m, 2 H). ¹³C NMR (125 MHz, CDCl₃): δ = 168.7, 168.6, 153.4, 153.3, 148.3, 146.8, 139.3, 133.5, 132.0, 131.5, 129.5, 128.9, 127.1, 126.4, 125.8, 125.7, 125.1, 123.4, 123.2, 115.4, 112.9, 112.7, 111.2, 111.0, 74.2, 70.9, 70.7, 67.3, 67.2, 38.6, 38.5. HR-ESI (MeOH): m/z [M + Na]⁺ calcd for C₃₁H₂₉N₂O₇ ⁷⁹BrNa: 643.1050, found: 643.1039. Anal. Calcd for C₃₁H₂₉N₂O₇Br: C, 59.91; H, 4.70; N, 4.51; Br, 12.86. Found: C, 60.01; H, 4.84; N, 4.38; Br, 12.74.

18

HPLC analyses for 11 and 12. Column: Chiralcel OD-H^®, length 250 mm; i.d. 4.6 mm. For 11: i-PrOH-hexane, 3:1; flow rate 0.7 mL/min.; λ = 254 nm. For 12: i-PrOH-hexane, 1:1; flow rate 1.1 mL/min.; λ = 254 nm. Enantiomeric purities obtained: (+)11: 93% ee, [α]_D ²⁶ = +61.8 (c = 0.56, CHCl₃); (-)11: 88% ee, [α]_D ²⁶ -59.3 (c = 0.55, CHCl₃); (+)12: 99% ee, [α]_D ²⁶ = +18.9 (c = 0.37, CHCl₃); (-)12: 94% ee, [α]_D ²⁶ -17.9 (c = 0.37, CHCl₃).

19

CD experiments were measured in MeCN in a 0.1 cm cell at 24 °C.