Stereoselective nucleophilic addition with a new chiral template and its application to the synthesis of optically active α-arylglycine derivatives

Synthesis

Volumn , Issue 6, 2004, Pages 909-917

  Tohma, Shigemitsu ^a   Rikimaru, Kentaro ^a   Endo, Atsushi ^a   Shimamoto, Keiko ^b   Kan, Toshiyuki ^a   Fukuyama, Tohru ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b SUNTORY INSTITUTE FOR BIOORGANIC RESEARCH   (Japan)

Author keywords

Amino acids; Arylboronic acids; Electron rich aromatics; Hydroxyphenylglycines; Iminolactone; Mannich type reaction; Phenols; arylglycines

Indexed keywords

ADDITION REACTIONS; AMINO ACIDS; ELECTRONS; PHENOLS; STEREOCHEMISTRY;

MANNICH-TYPE REACTIONS; NUCLEOPHILIC ADDITION;

SYNTHESIS (CHEMICAL);

3 (1H INDOL 3 YL) 6,6 DIMETHYL 5 PHENYLMORPHOLIN 2 ONE; 3 (2 HYDROXY 5 METHYLPHENYL) 6,6 DIMETHYL 5 PHENYLMORPHOLIN 2 ONE; 3 (2,4 DIMETHOXY 3 METHYLPHENYL) 6,6 DIMETHYL 5 PHENYLMORPHOLIN 2 ONE; 3 (4 AMINOPHENYL) 6,6 DIMETHYL 5 PHENYLMORPHOLIN 2 ONE; 3 (4 HYDROXY 3 METHYLPHENYL) 6,6 DIMETHYL 5 PHENYLMORPHOLIN 2 ONE; 3 (4 HYDROXYPHENYL) 6,6 DIMETHYL 5 PHENYLMORPHOLIN 2 ONE; 3 (5 BROMO 2 HYDROXYPHENYL) 6,6 DIMETHYL 5 PHENYLMORPHOLIN 2 ONE; 3 (5 HYDROXY 2,4 DIMETHOXY 3 METHYLPHENYL) 6,6 DIMETHYL 5 PHENYLMORPHOLIN 2 ONE; 3 [7 HYDROXY 6 (METHYLSULFONYL)OXY 1,3 BENZODIOXOL 4 YL] 6,6 DIMETHYL 5 PHENYLMORPHOLIN 2 ONE; 6,6 DIMETHYL 5 PHENYL 3 (2,4,6 TRIMETHOXYPHENYL)MORPHOLIN 2 ONE; AMINO ACID DERIVATIVE; AROMATIC COMPOUND; GLYCINE DERIVATIVE; LEWIS ACID; MORPHOLINE DERIVATIVE; PHENOL DERIVATIVE; PHENYLGLYCINE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; MANNICH REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 2342652148     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-815980     Document Type: Article

References (30)

1. Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon Press: Oxford, 1989.
2. For a review of asymmetric syntheses of arylglycines see: Williams, R. M.; Hendrix, J. A. Chem. Rev. 1992, 92, 889.
3. Watkins, J.; Collingridge, G. Trends Pharm. Sci. 1994, 15, 333.
4. (a) Bendingfield, J. S.; Kemp, M. C.; Jane, D. E.; Tse, H. W.; Roberts, P. J.; Watkins, J. C. Br. J. Pharmacol. 1995, 116, 3323.
5. (b) Sekiyama, N.; Hayashi, Y.; Nakanishi, S.; Jane, D. E.; Tse, H. W.; Birse, E. F.; Watkins, J. C. Br J Pharmacol. 1996, 117, 1493.
6. (c) Hayashi, Y.; Sekiyama, N.; Nakanishi, S.; Jane, D. E.; Sunter, D. C.; Birse, E. F.; Udvarhelyi, P. M.; Watkins, J. C. J. Neurosci. 1994, 14, 3370.
7. (a) Evans, D. A.; Britton, T. C.; Dorow, R. L.; Dellaria, J. F. J. Am. Chem. Soc. 1986, 108, 6395.
8. (b) Evans, D. A.; Britton, T. C.; Dorow, R. L.; Dellaria, J. F. Tetrahedron 1988, 44, 5525.
9. Caron, M.; Carlier, P. R.; Sharpless, K. B. J. Org. Chem. 1988, 53, 5185.
10. Williams, R. M.; Hendrix, J. A. J. Org. Chem. 1990, 55, 3723.
11. Endo, A.; Kan, T.; Fukuyama, T. Synlett 1999, 1103.
12. For the first report of the iminolactone 4 see: (a) Tohma, S.; Endo, A.; Kan, T.; Fukuyama, T. Synlett 2001, 1179. (b) and for its application to the total synthesis of ecteinascidin 743, see: Endo, A.; Yanagisawa, A.; Abe, M.; Tohma, S.; Kan, T.; Fukuyama, T. J. Am. Chem. Soc. 2002, 124, 6552.
13. For the first report of the iminolactone 4 see: (a) Tohma, S.; Endo, A.; Kan, T.; Fukuyama, T. Synlett 2001, 1179. (b) and for its application to the total synthesis of ecteinascidin 743, see: Endo, A.; Yanagisawa, A.; Abe, M.; Tohma, S.; Kan, T.; Fukuyama, T. J. Am. Chem. Soc. 2002, 124, 6552.
14. (a) During the course of this investigation the preparation of the iminolactone B from phenylglycinol A and reaction with a Grignard reagent was reported: Harwood, L. M.; Tyler, S. N. G.; Anslow, A. S.; MacGlip, I. D.; Drew, M. G. B. Tetrahedron: Asymmetry 1997, 8, 4007.
15. (b) Similar iminolactones were prepared from 2-substituted oxazolines see: Shafer, C. M.; Molinski, T. F. J. Org. Chem. 1996, 61, 2044.
16. (c) For its application to Mannich-type reactions see: Chen, Y.-J.; Lei, F.; Liu, L.; Wang, D. Tetrahedron 2003, 59, 7609. (Equation Presented)
17. (a) For preparation of the phenol 5a see: Fukuyama, T.; Sachleben, R. A. J. Am. Chem. Soc. 1982, 104, 4957.
18. (b) For preparation of phenols 5b see: ref. 6
19. 3N in 85% yield. X-ray crystallographic data for the structure reported in this paper have been deposited with the Cambridge Crystallographic Date Base (Deposition No. 162231). Copies of the data can be obtained free of charge on application to the CCDC 12 Union Road, Cambridge CB21EZ UK [fax 444 (1223)336333; E-mail: deposit@ccdc.cam.ac.uk].
20. Petasis, N. A.; Goodman, A.; Zavialov, I. A. Tetrahedron 1997, 48, 16463.
21. (a) Ishiyama, T.; Miyaura, N. J. Synth. Org. Chem., Jpn. 1999, 57, 503.
22. (b) Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2000, 611, 392.
23. Unfortunately the hydroxyphenylglycines 17a-c had no agonist and antagonist activity in mGluR1-5. Detailed experimental procedures and results of the assay will be reported elsewhere.
24. 2-Hydroxypyridine is a weak acid (pKa 11.7), used for the conversion of aliphatic esters to the corresponding amides, see: (a) Openshaw, H. T.; Whittaker, N. J. Chem. Soc. (C) 1969, 89. (b) Kametani, T.; Kanaya, N.; Ihara, M. J. Chem. Soc., Perkin Trans. 1 1981, 959. (c) Jagers, E.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1981, 20, 1016. (d) Raduchel, B. Tetrahedron Lett. 1983, 24, 3229. (e) Hoffmann, R. W.; Eudesfelder, A. Liebigs Ann. Chem. 1986, 1823.
25. 2-Hydroxypyridine is a weak acid (pKa 11.7), used for the conversion of aliphatic esters to the corresponding amides, see: (a) Openshaw, H. T.; Whittaker, N. J. Chem. Soc. (C) 1969, 89. (b) Kametani, T.; Kanaya, N.; Ihara, M. J. Chem. Soc., Perkin Trans. 1 1981, 959. (c) Jagers, E.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1981, 20, 1016. (d) Raduchel, B. Tetrahedron Lett. 1983, 24, 3229. (e) Hoffmann, R. W.; Eudesfelder, A. Liebigs Ann. Chem. 1986, 1823.
26. 2-Hydroxypyridine is a weak acid (pKa 11.7), used for the conversion of aliphatic esters to the corresponding amides, see: (a) Openshaw, H. T.; Whittaker, N. J. Chem. Soc. (C) 1969, 89. (b) Kametani, T.; Kanaya, N.; Ihara, M. J. Chem. Soc., Perkin Trans. 1 1981, 959. (c) Jagers, E.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1981, 20, 1016. (d) Raduchel, B. Tetrahedron Lett. 1983, 24, 3229. (e) Hoffmann, R. W.; Eudesfelder, A. Liebigs Ann. Chem. 1986, 1823.
27. 2-Hydroxypyridine is a weak acid (pKa 11.7), used for the conversion of aliphatic esters to the corresponding amides, see: (a) Openshaw, H. T.; Whittaker, N. J. Chem. Soc. (C) 1969, 89. (b) Kametani, T.; Kanaya, N.; Ihara, M. J. Chem. Soc., Perkin Trans. 1 1981, 959. (c) Jagers, E.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1981, 20, 1016. (d) Raduchel, B. Tetrahedron Lett. 1983, 24, 3229. (e) Hoffmann, R. W.; Eudesfelder, A. Liebigs Ann. Chem. 1986, 1823.
28. 2-Hydroxypyridine is a weak acid (pKa 11.7), used for the conversion of aliphatic esters to the corresponding amides, see: (a) Openshaw, H. T.; Whittaker, N. J. Chem. Soc. (C) 1969, 89. (b) Kametani, T.; Kanaya, N.; Ihara, M. J. Chem. Soc., Perkin Trans. 1 1981, 959. (c) Jagers, E.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1981, 20, 1016. (d) Raduchel, B. Tetrahedron Lett. 1983, 24, 3229. (e) Hoffmann, R. W.; Eudesfelder, A. Liebigs Ann. Chem. 1986, 1823.
29. 2 in MeOH (see also ref.18).
30. 2O in moderate yield (41% from methyl ester hydrochloride): Davies, S. G.; Polywka, M. E. C.; Sanganee, H. J. US 005801249A, 1998.