Efficient Synthesis of New Macrocycles with Planar Chirality

Jarosław Kalisiak; Janusz Jurczak

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;

Abstract

Alle Artikel dieser Rubrik

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

Volltext

Referenzen

References

1a Bolm C. Muniz K. Chem. Soc. Rev. 1999, 28: 51

1b Deng W.-P. You S.-L. Hou X.-L. Dai L.-X. Yu Y.-H. Xia W. Sun J. J. Am Chem. Soc. 2001, 123: 6508

For reviews, see:

2a Ferrocenes Togni A. Hayashi T. VCH; Weinheim: 1995.

2b Richards CJ. Locke AJ. Tetrahedron: Asymmetry 1998, 9: 2377

2c Togni A. Bieler N. Burckhardt U. Köllner C. Pioda G. Schneider R. Schnyder A. Pure Appl. Chem. 1999, 71: 1531

2d Dai L.-X. Hou X.-L. Deng W.-P. You S.-L. Zhou Y.-G. Pure Appl. Chem. 1999, 71: 1401

3a Tye H. Comina PJ. J. Chem. Soc., Perkin Trans. 1 2001, 1729

3b Farrell A. Goddard R. Guiry PJ. J. Org. Chem. 2002, 67: 4209

3c You S.-L. Hou X.-L. Dai L.-X. Yu Y.-H. Xia W. J. Org. Chem. 2002, 67: 4684

4 Gibson SE. Ibrahim H. Chem. Commun. 2002, 21: 2465

5a Gibson SE. Knight JD. Org. Biomol. Chem. 2003, 1: 1256

5b Rozenberg V. Kharitonov V. Antonov D. Sergeeva E. Aleshkin A. Ikonnikov N. Orlova S. Belokon Y. Angew. Chem., Int. Ed. Engl. 1994, 33: 91

5c Pye PJ. Rossen K. Reamer RA. Tsou NN. Volante RP. Reider PJ. J. Am. Chem. Soc. 1997, 119: 6207

5d Dahmen S. Bräse S. J. Am. Chem. Soc. 2002, 124: 5940

5e Wu X.-W. Yuan K. Sun W. Zhang M.-J. Hou X.-L. Tetrahedron: Asymmetry 2003, 14: 107

6a Lüttringhaus A. Gralheer H. Justus Liebigs Ann. Chem. 1942, 550: 67

6b Lüttringhaus A. Gralheer H. Justus Liebigs Ann. Chem. 1947, 557: 108

6c Lüttringhaus A. Gralheer H. Justus Liebigs Ann. Chem. 1947, 557: 112

For reviews, see:

7a Vögtle F. Neumann P. Top. Curr. Chem. 1974, 48: 67

7b Vögtle F. Hohner G. Top. Curr. Chem. 1978, 74: 1

7c Boekelheide V. Acc. Chem. Res. 1980, 13: 65

7d Collet A. Dutasta J.-P. Lozach B. Canceill J. Top. Curr. Chem. 1993, 165: 103

8a Vögtle F. Meurer K. Mannschreck A. Stühler G. Puff H. Roloff A. Sievers R. Chem. Ber. 1983, 116: 2630

8b Kang GJ. Chan TH. J. Org. Chem. 1985, 50: 452

8c Meurer K. Luppertz F. Vögtle F. Chem. Ber. 1985, 118: 4433

8d Grimme S. Pischel I. Vögtle F. Nieger M. J. Am. Chem. Soc. 1995, 117: 157

8e Hochmuth DH. König WA. Liebigs Ann. 1996, 947

8f Müller D. Böhme M. Nieger M. Rissanen K. Vögtle F. J. Chem. Soc., Perkin Trans. 1 1996, 2937

8g Grimme S. Harren J. Sobański A. Vögtle F. Eur. J. Org. Chem. 1998, 1491

8h Iwamoto H. Yang Y. Usui S. Fukazawa Y. Tetrahedron Lett. 2001, 42: 49

8i Es DS. Gret N. Rijke M. Eis MJ. Kanter FJJ. Wolf WH. Bickelhaupt F. Menzer S. Spek AL. Tetrahedron 2001, 57: 3557

9a Schmidtchen FP. Berger M. Chem. Rev. 1997, 97: 1609

9b Kubik S. Goddard R. J. Org. Chem. 1999, 64: 9475

9c Piątek P. Jurczak J. Chem. Commun. 2002, 2450

9d Bondy CR. Loeb SJ. Coord. Chem. Rev. 2003, 240: 77

9e Choi K. Hamilton AD. Coord. Chem. Rev. 2003, 240: 101

10a Gryko DT. Gryko D. Jurczak J. Synlett 1999, 1310

10b Piątek P. Gruza MM. Jurczak J. Tetrahedron: Asymmetry 2001, 12: 1763

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.

12 Yu MJ. McCowan JR. Phebus LA. Towner RD. Ho PPK. Keith PT. Luttman CA. Saunders RD. Ruterbories KJ. Lindstrom TD. Wikel JH. Morgan E. Hahn RA. J. Med. Chem. 1993, 36: 1262

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.

14 Gryko DT. Piątek P. Jurczak J. Tetrahedron 1997, 53: 7957

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.

16 Piątek P. Kalisiak J. Jurczak J. Tetrahedron Lett. 2004, 45: 3309

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.