A versatile approach for the asymmetric synthesis of 3-alkyl-2,3-dihydro- 1H-isoindolin-1-ones

Tetrahedron

Volumn 60, Issue 7, 2004, Pages 1651-1657

  Chen, Ming De ^a   Zhou, Xiang ^a   He, Ming Zhu ^a   Ruan, Yuan Ping ^a   Huang, Pei Qiang ^a  

^a XIAMEN UNIVERSITY   (China)

Author keywords

Asymmetric synthesis; Benzyloxyphenylglycinol; Chiral auxiliary; Isoindolin 1 one

Indexed keywords

4 BENZYLOXYPHENYLGLYCINOL; GLYCINE DERIVATIVE; ISOINDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION; PRIORITY JOURNAL; REDUCTION; STEREOCHEMISTRY;

EID: 0742306819     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.11.092     Document Type: Article

References (61)

1. Belliotti T.R., Brink W.A., Kesten S.R. Bioorg. Med. Chem. Lett. 8:1998;1499-1502.
2. Wada T., Fukuda N. Psychopharmacology. 103:1991;314-322.
3. Kavoussi R.J., Pande A.C., Lydiard R.B., Pap L., Pigott T.A., Rickels K. Int. J. Neuropsychopharmacol. 3:(Suppl. 1):2000;. Abst. P. 09.042.
4. Fuchs J.R., Funk R.L. Org. Lett. 3:2001;3923-3925.
5. Oppolzer W., Wills M., Kelly M.J., Signer M., Blagg J. Tetrahedron Lett. 31:1990;5015-5018.
6. Murphy J.P., Nieuwenhuyzen M., Reynolds K., Sarma P.K.S., Stevenson P.J. Tetrahedron Lett. 36:1995;9533-9536.
7. McAlonan H., Murphy J.P., Nieuwenhuyzen M., Reynolds K., Sarma P.K.S., Stevenson P.J., Thompson N. J. Chem. Soc., Perkin Trans. 1. 2002;69-79.
8. Hunter R., Richards P. Tetrahedron Lett. 41:2000;3755-3758.
9. Kundu N.G., Khan M.W. Tetrahedron. 56:2000;4777-4792.
10. Epsztajn J., Jozwiak A., Koluda P., Sadokierska I., Wilkowska I.D. Tetrahedron. 56:2000;4837-4844.
11. Hoarau C., Couture A., Deniau E., Grandclaudon P. Synthesis. 2000;655-660.
12. Deniau E., Enders D. Tetrahedron Lett. 41:2000;2347-2350.
13. Yoda H., Matsuda K., Nomura H., Takabe K. Tetrahedron Lett. 41:2000;1775-1779.
14. Koseki Y., Kusano S., Sakata H., Nagasaka T. Tetrahedron Lett. 40:1999;2169-2172.
15. Luzzio F.A., Zacherl D.P. Tetrahedron Lett. 39:1998;2285-2288.
16. Deniau E., Enders D. Tetrahedron. 57:2001;2581-2588.
17. Allin S.M., Northfield C.J., Page M.I., Slawin A.M.Z. J. Chem. Soc., Perkin Trans. 1. 2000;1715-1721. and references cited therein.
18. Enders D., Braig V., Raabe G. Can. J. Chem. 79:2001;1528-1535.
19. Ukaji Y., Tsukamoto K., Nasada Y., Shimizu M., Fujisawa T. Chem. Lett. 1993;221-224.
20. Pérard-Viret J., Prangé T., Tomas A., Royer J. Tetrahedron. 58:2002;5103-5108.
21. Chen M.D., He M.Z., Huang L.Q., Ruan Y.P., Huang P.-Q. Chin. J. Chem. 20:2002;1149-1153.
22. This work was taken in part from the Master theses of He, M. Z., Xiamen University, China, 2003.
23. For reviews on the use of (R)-phenylglycinol as a chiral auxiliary, see: (a) Husson H.P., Royer. J. Chem. Soc. Rev. 28:1999;383-394.
24. Groaning M.D., Meyers A.I. Tetrahedron. 56:2000;9843-9873.
25. Eleveld M.B., Hogeveen H., Schudde E.P. J. Org. Chem. 51:1986;3635-3642.
26. Andres C., Gonzalez A., Pedrosa R., Perezs-Encabo A., Garcia-Granda S., Salvado M.A., Gomez-Beltran F. Tetrahedron Lett. 33:1992;4743-4746.
27. Harwood L.M., Macro J., Watkin D., Williams C.E., Wong L.F. Tetrahedron: Asymmetry. 3:1992;1127-1130.
28. Harder T., Lohl T., Bolte M., Wagner K., Hoppe D. Tetrahedron Lett. 35:1994;7365-7368.
29. Agami C., Couty F., Hamon L., Venier O. J. Org. Chem. 62:1997;2106-2112.
30. Carrillo L., Badia D., Dominguez E., Vicario J.L., Tellitu I. J. Org. Chem. 62:1997;6716-6721.
31. Steinig A.G., Spero D.M. J. Org. Chem. 64:1999;2406-2410.
32. Adam W., Peters K., Peters E.M., Schambony S.B. J. Am. Chem. Soc. 122:2000;7610-7611.
33. Cevallos A., Rios R., Moyano A., Pericas M.A., Riera A. Tetrahedron: Asymmetry. 11:2000;4407-4416.
34. Chakraborty T.K., Reddy G.V., Hussain K.A. Tetrahedron Lett. 32:1991;7597-7600.
35. Spero D.M., Kapadia S.R. J. Org. Chem. 62:1997;5537-5541.
36. Pridgen L.N., Mokhallalati M.K., Wu. J. Org. Chem. 57:1992;1237-1241.
37. Chen L., Trilles R.V., Tilley J.W. Tetrahedron Lett. 36:1995;8715-8718.
38. Chakraborty T.K., Hussain K.A., Reddy G.V. Tetrahedron. 51:1995;9179-9190.
39. Delorme D., Berthelette C., Lavoie R., Roberts E. Tetrahedron: Asymmetry. 9:1998;3963-3966.
40. Blanchet J., Bonin M., Micouin L., Husson H.P. J. Org. Chem. 65:2000;6423-6426.
41. Chang Z.Y., Coates R.M. J. Org. Chem. 55:1990;3475-3483.
42. Mehmandoust M., Marazano C., Das B.C. J. Chem. Soc., Chem. Commun. 1989;1185-1187.
43. Agami C., Couty F., Evano G. Tetrahedron Lett. 40:1999;3709-3712.
44. Julina R., Herzig T., Bernet B., Vasella A. Helv. Chim. Acta. 69:1986;368-373.
45. Fains O., Vernon J.M. Tetrahedron Lett. 38:1997;8265-8266.
46. Nyzam V., Belaud C., Zammatio F., Villieras J. Tetrahedron: Asymmetry. 7:1996;1835-1843.
47. Burgess L.E., Meyers A.I. J. Org. Chem. 57:1992;1656-1662.
48. Greene T.W., Wuts P.G.M. Protective groups in organic chemistry. 2nd ed. 1991;Wiley, New York. p 401.
49. Yamaura M., Suzuki T., Hashimoto H., Yoshimura J., Okamoto T., Shin C. Bull. Chem. Soc. Jpn. 58:1985;1413-1420.
50. Yoshimura J., Yamaura M., Suzuki T., Hashimoto H. Chem. Lett. 1983;1001-1002.
51. Ma D., Tian H. J. Chem. Soc., Perkin Trans. 1. 1997;3493-3496.
52. Kumar G.B., Shah A.C., Pilati T. Tetrahedron Lett. 38:1997;3297-3300.
53. For a recent review, see: Speckamp W.N., Moolenaar M.J. Tetrahedron. 56:2000;3817-3856.
54. Kursanov D.N., Parnes Z.N., Loim N.M. Synthesis. 1974;633-651.
55. Nagai Y. Org. Prep. Proc. Int. 12:1980;13-48.
56. Hart D.J., Yang T.-K. J. Org. Chem. 50:1985;235-242.
57. Rolf D., Gray G.R. J. Am. Chem. Soc. 104:1982;3539-3541.
58. During the submission of the present manuscript, Enders and co-workers reported a new flexible approach to (R)-3-substituted-2,3-dihydro-1H-isoindolin- 1-ones based on a new oxidatively cleavable chiral auxiliary, and one more previously unknown enantiomerically enriched (R)-3-tert-butyl-2,3-dihydro-1H- isoindolin-1-one were reported Deniau E., Enders D., Couture A., Grandclaudon P. Tetrahedron: Asymmetry. 14:2003;2253-2258.
59. Helberger J.H., Hevér D.B. Justus Liebigs Ann. Chem. 536:1938;173-179.
60. Bromberg O. Chem. Ber. 29:1896;1434-1442.
61. Wöelbling H. Chem. Ber. 38:1905;3925-3928.