Highly Diastereoselective Synthesis of 3-Indolyl-N-Substituted Glycine Derivatives via TFA-Promoted Friedel-Crafts Type Reaction of Indoles with Chiral Cyclic Glyoxylate Imine

Fei Lei; Yong-Jun Chen; Yong Sui; Li Liu; Dong Wang

doi:10.1055/s-2003-39905

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synlett 2003(8): 1160-1164
DOI: 10.1055/s-2003-39905

LETTER

Highly Diastereoselective Synthesis of 3-Indolyl-N-Substituted Glycine Derivatives via TFA-Promoted Friedel-Crafts Type Reaction of Indoles with Chiral Cyclic Glyoxylate Imine

Fei Lei, Yong-Jun Chen*, Yong Sui, Li Liu, Dong Wang*
Laboratory of Chemical Biology, Center for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100080, China
e-Mail: dwang210@iccas.ac.cn;

Further Information

Publication History

Received 24 March 2003
Publication Date:
11 June 2003 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

A method based on the highly diastereoselective Friedel-Crafts type reaction of indoles with chiral cyclic glyoxylate imines in the presence of TFA toward the stereoselective synthesis of 3-indolyl-N-substituted glycine derivatives is presented. The absolute configuration of the newly formed chiral center was determined by a single-crystal X-ray analysis.

Key words

Friedel-Crafts reaction - Brönsted acid - chiral cyclic glyoxylate imines - optically active indolyglycines

References

1a Najera C. Synlett 2002, 9: 1388

Google Scholar
1b Williams RM. Hendrix JA. Chem. Rev. 1992, 92: 889

Google Scholar
1c Williams RM. Aldrichimica Acta 1992, 11

Google Scholar
1d Duthaler RO. Tetrahedron 1994, 50: 1539

Google Scholar
1e Shen TY. inventors; US Patent, 3316260.
1f Blaszczak LC, and Turner JR. inventors; EP 122157.
1g Clark BP. Harris JR. Synth. Commun. 1997, 27: 4223

Google Scholar
2a Kawasaki T. Ohno K. Enoki H. Umemoto Y. Sakamoto M. Tetrahedron Lett. 2002, 43: 4245

Crossref Google Scholar
2b Kawasaki T. Enoki H. Matsumura K. Ohyama M. Inagawa M. Sakamoto M. Org. Lett. 2000, 2: 3027

Crossref Google Scholar
2c Yang CG. Wang J. Tang XX. Jiang B. Tetrahedron: Asymmetry 2002, 13: 383

Crossref Google Scholar
3a Humber LG. Ferdinandi E. Demerson CA. Ahmed S. Shah U. Mobilio D. Sabatucci J. De Lange B. Labbadia F. Hughes P. DeVigilio J. Neuman G. Chau TT. Weichman BM. J. Med. Chem. 1988, 31: 1712

Crossref Google Scholar
3b Katz AH. Demerson CA. Shaw CC. Asselin AA. Humber LG. Conway KM. Gavin G. Guinosso C. Jensen NP. Mobilio D. Noureldin R. Schmid J. Shah U. Van Engen D. Chau TT. Weichman BM. J. Med. Chem. 1988, 31: 1244

Crossref Google Scholar
4 Blaszczak LC, and Turner JP. inventors; US Patent, 4492694.
5a Sakai N. Hirasawa M. Hamajima T. Konakahara T. J. Org. Chem. 2003, 68: 483

Article in Thieme Connect Google Scholar
5b Sakai N. Hamajima T. Konakahara . Tetrahedron Lett. 2002, 43: 4821

Article in Thieme Connect Google Scholar
5c Janczuk A. Zhang W. Xie WH. Lou SZ. Cheng JP. Wang PG. Tetrahedron Lett. 2002, 43: 4271

Article in Thieme Connect Google Scholar
5d Wynne JH. Stalick WM. J. Org. Chem. 2002, 67: 5850

Article in Thieme Connect Google Scholar
5e Hao J. Taktak S. Aikawa K. Yusa Y. Hatano M. Mikami K. Synlett 2001, 1443

Article in Thieme Connect Google Scholar
5f Xie WH. Bloomfield KM. Jin YF. Dolney NY. Wang PG. Synlett 1999, 498

Article in Thieme Connect Google Scholar
6a Jiang B. Yang CG. Gu XH. Tetrahedron Lett. 2001, 42: 2545 ; and references cited therein

Crossref Google Scholar
6b Corey EJ. Gorgan MJ. Org. Lett. 1999, 1: 157

Crossref Google Scholar
6c Ishitani H. Komiyama S. Kobayashi S. Angew. Chem. Int. Ed. 1998, 37: 3186

Crossref Google Scholar
6d Iyer MS. Gigstad KM. Namdev ND. Lipton M. J. Am. Chem. Soc. 1996, 118: 4910

Crossref Google Scholar
7 Johannsen M. Chem. Commun. 1999, 2233

Google Scholar
8a Ferraris D. Young B. Dudding T. Drury WJ. Lectka T. Tetrahedron 1999, 55: 8869

Crossref Google Scholar
8b Ferraris D. Dudding T. Young B. William JD. Lectka T. J. Org. Chem. 1999, 64: 2168

Crossref Google Scholar
9a Petasis NA. Goodman A. Zavialov IA. Tetrahedron 1997, 48: 16463

Crossref Google Scholar
9b Petasis NA. Zavialov IA. J. Am. Chem. Soc. 1997, 119: 445

Crossref Google Scholar
9c Petasis NA. Boral S. Tetrahedron Lett. 2001, 42: 539

Crossref Google Scholar
10a Olah GA. Friedel-Crafts and Related Reactions Vol. III: Interscience; New York: 1964. Part 1.

Google Scholar
10b Heaney H. In Comprehensive Organic Synthesis Trost BM. Pergamon Press; New York: 1991.

Google Scholar
11a Ueda M. Miyabe H. Teramachi M. Miyata O. Naito T. Chem. Commun. 2003, 426

Article in Thieme Connect Google Scholar
11b Bertrand MP. Coantic S. Feray L. Nouguier R. Perfetti P. Tetrahedron 2000, 56: 3951

Article in Thieme Connect Google Scholar
11c Bertrand MP. Feray L. Nouguier R. Stella L. Synlett 1998, 780

Article in Thieme Connect Google Scholar
11d Harwood LM. Tyler SNG. Anslow AS. MacGilp ID. Drew MGB. Tetrahedron: Asymmetry 1997, 8: 4007

Article in Thieme Connect Google Scholar
11e Harwood LM. Vines KJ. Drew MGB. Synlett 1996, 1051

Article in Thieme Connect Google Scholar
12a Tohma S. Endo A. Kan T. Fukuyama T. Synlett 2001, 1179

Article in Thieme Connect Google Scholar
12b Endo A. Yanagisawa A. Abe M. Tohma S. Kan T. Fukuyama T. J. Am. Chem. Soc. 2002, 124: 6552

Article in Thieme Connect Google Scholar
12c Endo A. Kan T. Fukuyama T. Synlett 1999, 1103

Article in Thieme Connect Google Scholar
13a Snyder HR. Matteson DS. J. Am. Chem. Soc. 1957, 79: 2217

Google Scholar
13b Van Tamelen EE. Knapp GC. J. Am. Chem. Soc. 1955, 77: 1860

Google Scholar
14a Ottoni O. de V. F. Neder A. Dias AKB. Cruz RP. Aquino LB. Org. Lett. 2001, 3: 1005

Crossref PubMed Google Scholar
14b Okauchi T. Itonaga M. Minami T. Owa T. Kitoh K. Yoshino H. Org. Lett. 2000, 2: 1485

Crossref PubMed Google Scholar
15a Chen YJ. Ge CS. Wang D. Synlett 2000, 1429

Article in Thieme Connect Google Scholar
15b Ge CS. Zhang J. Chen YJ. Wang D. Acta Chimica Sinica 2001, 59: 1835

Article in Thieme Connect Google Scholar
15c Ge CS. Chen YJ. Wang D. Synlett 2002, 37

Article in Thieme Connect Google Scholar
16 Shafer CM. Molinski TF. J. Org. Chem. 1996, 61: 2044

Crossref Google Scholar
17 Meyers AI. Knaus G. Kamata K. Ford ME. J. Am. Chem. Soc. 1976, 98: 567

Crossref Google Scholar
21 Ishii H. Murakami K. Sakurada E. Hosoya K. Murakami Y. J. Chem. Soc., Perkin Trans. 1 1988, 2377

Google Scholar
Several methods have existed for the removal of the chiral template from the similar compounds without notable racemization:
22a Aldous DJ. Drew MGB. Hamelin EM.-N. Harwood LM. Jahana AB. Thurairatnam S. Synlett 2001, 1836

Google Scholar
22b Cox GG. Harwood LM. Tetrahedron: Asymmetry 1994, 5: 1669

Google Scholar
22c Harwood LM. Macro J. Watkin D. Williams E. Wong LF. Tetrahedron: Asymmetry 1992, 3: 1127 ; and also refs.

Google Scholar
22d
Although we did not study this issue systematically, the preliminary result showed that when 3bc was subjected to the hydrogenolysis in aqueous methanol using Pearlman’s catalyst [Pd(OH)₂/C] and TFA under 1 atmosphere of hydrogen gas for 5 h, the corresponding optically active amino acid was obtained in 82% yield, [α]_D ²⁰ +57 (c 0.35, CH₃OH).

Google Scholar

18

Representative experimental procedure: To a solution of indole (1.2 equiv) and chiral cyclic glyoxylate imine (1.0 equiv) in CH₂Cl₂ at 0 °C, TFA (5 equiv) was added dropwise by syringe. After the reaction mixture was stirred for 3 h at 0 °C, usual work-up furnished a residue from which the pure product was obtained after purification with flash chromatography on silica gel [all new compounds were subjected to ¹H NMR, ¹³C NMR, IR, MS(FAB) analysis]. The diastereoselectivity was determined by ¹H NMR and ¹³C NMR spectra. All compounds gave satisfactory spectral data. Selected data for compound 3c*: mp: 234-236 °C, [α]_D ²⁰ +148.57 (c 0.7, acetone); FTIR (KBr) 3338, 1734, 1693, 1538, 1454, 1377, 1343, 1319, 1256, 1217, 1190, 1086, 1014 cm^-1; ¹H NMR(300 Hz, CDCl₃): δ 1.38 (t, J = 7 Hz 3 H), 2.54 (br s, 1 H), 4.43 (m, 2 H), 4.90 (d, J = 4 Hz,
1 H), 5.90 (s, 1 H), 6.14 (d, J = 4 Hz, 1 H), 7.11-7.29 (m, 12 H), 7.39-7.45 (m, 2 H), 7.79 (d, J = 8 Hz, 1 H), 8.96 (br s,
1 H); ¹³C NMR(75 Hz, CDCl₃) δ 14.5, 52.8, 58.3, 61.6, 85.4, 113.4, 121.4, 121.8, 125.7, 126.0, 127.6, 128.2, 128.4, 128.6, 128.9, 129.3, 137.2, 138.0, 138.5, 162.3, 169.3; HRMS (FAB): m/z 441.1811 for [MH⁺] C₂₇H₂₅N₂O₄ requires 441.1808.

19

X-Ray analysis of 2c: The crystal used for the X-ray study had the dimensions 0.29 × 0.17 × 0.08 mm. Crystal data: C₁₆H₁₃NO₂, M 251.27; orthorhombic; space group, P2₁; lattice parameters, a = 5.9439 Å, b = 8.4943 Å, c = 25.5719 Å; V = 1291.11 Å³, Z = 4; D _calcd = 1.293 g/cm³; F ₀ = 528; number of reflections measured = 2737, l = 0.7107 Å.

20

X-Ray analysis of 3hc: The crystal used for the X-ray study had the dimensions 0.53 × 0.09 × 0.04 mm. Crystal data: C₂₄H₁₉BrN₂O₂, M 447.32; Monoclinic; space group, C₂; lattice parameters, a = 26.817 Å, b = 7.9070 Å, c = 9.8754 Å; V = 2083.1 Å³, Z = 4; D _calcd = 1.426 g/cm³; F ₀ = 912; number of reflections measured = 4268, l = 0.7107 Å.