SCOPUS 정보 검색 플랫폼

Volumn 39, Issue 51, 1998, Pages 9407-9410

Synthesis of chiral oxazolidin-2-ones and imidazolidin-2-ones via DMAP- catalyzed isocyanation of amines with di-tert-butyl dicarbonate

(2) Knölker, Hans Joachim a Braxmeier, Tobias a

a UNIVERSITY OF KARLSRUHE (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXAZOLIDINONE DERIVATIVE; BICARBONATE; IMIDAZOLIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION KINETICS; CHIRALITY; MOLECULAR RECOGNITION; REACTION ANALYSIS; SYNTHESIS;

EID: 0032542170 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(98)02194-7 Document Type: Article

Times cited : (58)

References (37)

1
- 0242371719
- 1. Part 4: H.-J. Knölker, T. Braxmeier, Synlett 1997, 925.
- (1997) Synlett , pp. 925
- Knölker, H.-J.¹ Braxmeier, T.²

2
- 0012016624
- 2. D. A. Evans, J. Bartroli, T. L. Shih, J. Am. Chem. Soc. 1981, 103, 2127; D. A. Evans, M. D. Ennis, D. J. Mathre, J. Am. Chem. Soc. 1982, 104, 1737; D. A. Evans, Aldrichimica Acta 1982, 15, 23; D. A. Evans, M. D. Ennis, T. Le, N. Mandel, G. Mandel, J. Am. Chem. Soc. 1984, 106, 1154. D. A. Evans, A. E. Weber, J. Am. Chem. Soc. 1986, 108, 6757; D. A. Evans, K. T. Chapman, J. Bisaha, J. Am. Chem. Soc. 1988, 110, 1238; D. A. Evans, T. C. Britton, R. L. Dorow, J. F. Dellaria, Jr, Tetrahedron 1988, 44, 5525.
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 2127
- Evans, D.A.¹ Bartroli, J.² Shih, T.L.³

3
- 33845554892
- 2. D. A. Evans, J. Bartroli, T. L. Shih, J. Am. Chem. Soc. 1981, 103, 2127; D. A. Evans, M. D. Ennis, D. J. Mathre, J. Am. Chem. Soc. 1982, 104, 1737; D. A. Evans, Aldrichimica Acta 1982, 15, 23; D. A. Evans, M. D. Ennis, T. Le, N. Mandel, G. Mandel, J. Am. Chem. Soc. 1984, 106, 1154. D. A. Evans, A. E. Weber, J. Am. Chem. Soc. 1986, 108, 6757; D. A. Evans, K. T. Chapman, J. Bisaha, J. Am. Chem. Soc. 1988, 110, 1238; D. A. Evans, T. C. Britton, R. L. Dorow, J. F. Dellaria, Jr, Tetrahedron 1988, 44, 5525.
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 1737
- Evans, D.A.¹ Ennis, M.D.² Mathre, D.J.³

4
- 0012016624
- 2. D. A. Evans, J. Bartroli, T. L. Shih, J. Am. Chem. Soc. 1981, 103, 2127; D. A. Evans, M. D. Ennis, D. J. Mathre, J. Am. Chem. Soc. 1982, 104, 1737; D. A. Evans, Aldrichimica Acta 1982, 15, 23; D. A. Evans, M. D. Ennis, T. Le, N. Mandel, G. Mandel, J. Am. Chem. Soc. 1984, 106, 1154. D. A. Evans, A. E. Weber, J. Am. Chem. Soc. 1986, 108, 6757; D. A. Evans, K. T. Chapman, J. Bisaha, J. Am. Chem. Soc. 1988, 110, 1238; D. A. Evans, T. C. Britton, R. L. Dorow, J. F. Dellaria, Jr, Tetrahedron 1988, 44, 5525.
- (1982) Aldrichimica Acta , vol.15 , pp. 23
- Evans, D.A.¹

5
- 33845471613
- 2. D. A. Evans, J. Bartroli, T. L. Shih, J. Am. Chem. Soc. 1981, 103, 2127; D. A. Evans, M. D. Ennis, D. J. Mathre, J. Am. Chem. Soc. 1982, 104, 1737; D. A. Evans, Aldrichimica Acta 1982, 15, 23; D. A. Evans, M. D. Ennis, T. Le, N. Mandel, G. Mandel, J. Am. Chem. Soc. 1984, 106, 1154. D. A. Evans, A. E. Weber, J. Am. Chem. Soc. 1986, 108, 6757; D. A. Evans, K. T. Chapman, J. Bisaha, J. Am. Chem. Soc. 1988, 110, 1238; D. A. Evans, T. C. Britton, R. L. Dorow, J. F. Dellaria, Jr, Tetrahedron 1988, 44, 5525.
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 1154
- Evans, D.A.¹ Ennis, M.D.² Le, T.³ Mandel, N.⁴ Mandel, G.⁵

6
- 0022490196
- 2. D. A. Evans, J. Bartroli, T. L. Shih, J. Am. Chem. Soc. 1981, 103, 2127; D. A. Evans, M. D. Ennis, D. J. Mathre, J. Am. Chem. Soc. 1982, 104, 1737; D. A. Evans, Aldrichimica Acta 1982, 15, 23; D. A. Evans, M. D. Ennis, T. Le, N. Mandel, G. Mandel, J. Am. Chem. Soc. 1984, 106, 1154. D. A. Evans, A. E. Weber, J. Am. Chem. Soc. 1986, 108, 6757; D. A. Evans, K. T. Chapman, J. Bisaha, J. Am. Chem. Soc. 1988, 110, 1238; D. A. Evans, T. C. Britton, R. L. Dorow, J. F. Dellaria, Jr, Tetrahedron 1988, 44, 5525.
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 6757
- Evans, D.A.¹ Weber, A.E.²

7
- 33845280186
- 2. D. A. Evans, J. Bartroli, T. L. Shih, J. Am. Chem. Soc. 1981, 103, 2127; D. A. Evans, M. D. Ennis, D. J. Mathre, J. Am. Chem. Soc. 1982, 104, 1737; D. A. Evans, Aldrichimica Acta 1982, 15, 23; D. A. Evans, M. D. Ennis, T. Le, N. Mandel, G. Mandel, J. Am. Chem. Soc. 1984, 106, 1154. D. A. Evans, A. E. Weber, J. Am. Chem. Soc. 1986, 108, 6757; D. A. Evans, K. T. Chapman, J. Bisaha, J. Am. Chem. Soc. 1988, 110, 1238; D. A. Evans, T. C. Britton, R. L. Dorow, J. F. Dellaria, Jr, Tetrahedron 1988, 44, 5525.
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 1238
- Evans, D.A.¹ Chapman, K.T.² Bisaha, J.³

8
- 0000744779
- 2. D. A. Evans, J. Bartroli, T. L. Shih, J. Am. Chem. Soc. 1981, 103, 2127; D. A. Evans, M. D. Ennis, D. J. Mathre, J. Am. Chem. Soc. 1982, 104, 1737; D. A. Evans, Aldrichimica Acta 1982, 15, 23; D. A. Evans, M. D. Ennis, T. Le, N. Mandel, G. Mandel, J. Am. Chem. Soc. 1984, 106, 1154. D. A. Evans, A. E. Weber, J. Am. Chem. Soc. 1986, 108, 6757; D. A. Evans, K. T. Chapman, J. Bisaha, J. Am. Chem. Soc. 1988, 110, 1238; D. A. Evans, T. C. Britton, R. L. Dorow, J. F. Dellaria, Jr, Tetrahedron 1988, 44, 5525.
- (1988) Tetrahedron , vol.44 , pp. 5525
- Evans, D.A.¹ Britton, T.C.² Dorow, R.L.³ Dellaria J.F., Jr.⁴

9
- 0027729991
- 3. D. A. Evans, H. P. Ng, D. L. Rieger, J. Am. Chem. Soc. 1993, 115, 11446.
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 11446
- Evans, D.A.¹ Ng, H.P.² Rieger, D.L.³

10
- 0025181123
- 4. T. K. Jones, R. A. Reamer, R. Desmond, S. G. Mills, J. Am. Chem. Soc. 1990, 112, 2998.
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 2998
- Jones, T.K.¹ Reamer, R.A.² Desmond, R.³ Mills, S.G.⁴

11
- 0000308076
- 5. H. Kubota, A. Kubo, M. Takahashi, R. Shimizu, T. Da-te, K. Okamura, K. Nunami, J. Org. Chem. 1995, 60, 6776.
- (1995) J. Org. Chem. , vol.60 , pp. 6776
- Kubota, H.¹ Kubo, A.² Takahashi, M.³ Shimizu, R.⁴ Da-te, T.⁵ Okamura, K.⁶ Nunami, K.⁷

12
- 0030880552
- 6. For a recent application, see: J. S. Madalengoita, J. J. Tepe, K. A. Werbovetz, E. K. Lehnert, T. L. Macdonald, Bioorg. Med. Chem. 1997, 5, 1807.
- (1997) Bioorg. Med. Chem. , vol.5 , pp. 1807
- Madalengoita, J.S.¹ Tepe, J.J.² Werbovetz, K.A.³ Lehnert, E.K.⁴ Macdonald, T.L.⁵

13
- 0030788368
- 7. For a recent application, see: J. S. Panek, P. Liu, Tetrahedron Lett. 1997, 38, 5127.
- (1997) Tetrahedron Lett. , vol.38 , pp. 5127
- Panek, J.S.¹ Liu, P.²

14
- 84987013623
- 8. F. Bracher, T. Litz, J. Prakt. Chem. 1995, 337, 516; L. Cotarca, P. Delogu, A. Nardelli, V. Sunjic, Synthesis 1996, 553; T. Akiba, O. Tamura, S. Terashima, Org. Synth. 1997, 75, 45.
- (1995) J. Prakt. Chem. , vol.337 , pp. 516
- Bracher, F.¹ Litz, T.²

15
- 0029899187
- 8. F. Bracher, T. Litz, J. Prakt. Chem. 1995, 337, 516; L. Cotarca, P. Delogu, A. Nardelli, V. Sunjic, Synthesis 1996, 553; T. Akiba, O. Tamura, S. Terashima, Org. Synth. 1997, 75, 45.
- (1996) Synthesis , pp. 553
- Cotarca, L.¹ Delogu, P.² Nardelli, A.³ Sunjic, V.⁴

16
- 0010408448
- 8. F. Bracher, T. Litz, J. Prakt. Chem. 1995, 337, 516; L. Cotarca, P. Delogu, A. Nardelli, V. Sunjic, Synthesis 1996, 553; T. Akiba, O. Tamura, S. Terashima, Org. Synth. 1997, 75, 45.
- (1997) Org. Synth. , vol.75 , pp. 45
- Akiba, T.¹ Tamura, O.² Terashima, S.³

17
- 0001274286
- 9. H. A. Staab, Angew. Chem. 1962, 74, 407; Angew. Chem. Int. Ed. Engl. 1962, 1, 351; K. Ishida, H. Matsuda, M. Murakami, K. Yamaguchi, Tetrahedron 1997, 53, 10281.
- (1962) Angew. Chem. , vol.74 , pp. 407
- Staab, H.A.¹

18
- 0001274285
- 9. H. A. Staab, Angew. Chem. 1962, 74, 407; Angew. Chem. Int. Ed. Engl. 1962, 1, 351; K. Ishida, H. Matsuda, M. Murakami, K. Yamaguchi, Tetrahedron 1997, 53, 10281.
- (1962) Angew. Chem. Int. Ed. Engl. , vol.1 , pp. 351

19
- 0030806260
- 9. H. A. Staab, Angew. Chem. 1962, 74, 407; Angew. Chem. Int. Ed. Engl. 1962, 1, 351; K. Ishida, H. Matsuda, M. Murakami, K. Yamaguchi, Tetrahedron 1997, 53, 10281.
- (1997) Tetrahedron , vol.53 , pp. 10281
- Ishida, K.¹ Matsuda, H.² Murakami, M.³ Yamaguchi, K.⁴

20
- 0000733886
- 10. G. Höfle, W. Steglich, H. Vorbrüggen, Angew. Chem. 1978, 90, 602; Angew. Chem. Int. Ed. Engl. 1978, 17, 569.
- (1978) Angew. Chem. , vol.90 , pp. 602
- Höfle, G.¹ Steglich, W.² Vorbrüggen, H.³

21
- 0017998510
- 10. G. Höfle, W. Steglich, H. Vorbrüggen, Angew. Chem. 1978, 90, 602; Angew. Chem. Int. Ed. Engl. 1978, 17, 569.
- (1978) Angew. Chem. Int. Ed. Engl. , vol.17 , pp. 569

22
- 0010369604
- German patent application P 19526081.3
- 11. H.-J. Knölker, T. Braxmeier, G. Schlechtingen, German patent application P 19526081.3, 1995; H.-J. Knölker, T. Braxmeier, G. Schlechtingen, Angew. Chem. 1995, 107, 2746; Angew. Chem. Int. Ed. Engl. 1995, 34, 2497.
- (1995)
- Knölker, H.-J.¹ Braxmeier, T.² Schlechtingen, G.³

23
- 0000904220
- 11. H.-J. Knölker, T. Braxmeier, G. Schlechtingen, German patent application P 19526081.3, 1995; H.-J. Knölker, T. Braxmeier, G. Schlechtingen, Angew. Chem. 1995, 107, 2746; Angew. Chem. Int. Ed. Engl. 1995, 34, 2497.
- (1995) Angew. Chem. , vol.107 , pp. 2746
- Knölker, H.-J.¹ Braxmeier, T.² Schlechtingen, G.³

24
- 33748223631
- 11. H.-J. Knölker, T. Braxmeier, G. Schlechtingen, German patent application P 19526081.3, 1995; H.-J. Knölker, T. Braxmeier, G. Schlechtingen, Angew. Chem. 1995, 107, 2746; Angew. Chem. Int. Ed. Engl. 1995, 34, 2497.
- (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 2497

25
- 0040935404
- 12. H.-J. Knölker, T. Braxmeier, G. Schlechtingen, Synlett 1996, 502.
- (1996) Synlett , pp. 502
- Knölker, H.-J.¹ Braxmeier, T.² Schlechtingen, G.³

26
- 0030581330
- 13. H.-J. Knölker, T. Braxmeier, Tetrahedron Lett. 1996, 37, 5861.
- (1996) Tetrahedron Lett. , vol.37 , pp. 5861
- Knölker, H.-J.¹ Braxmeier, T.²

27
- 0028568525
- 14. 1a, 1e, 1l: S. Iwama, S. Katsumura, Bull. Chem. Soc. Jpn. 1994, 67, 3363;
- (1994) Bull. Chem. Soc. Jpn. , vol.67 , pp. 3363
- Iwama, S.¹ Katsumura, S.²

28
- 0000184462
- 1b, 1e: L. N. Pridgen, J. Prol, B. Alexander, L. Gillyard, J. Org. Chem. 1989, 54, 3231;
- (1989) J. Org. Chem. , vol.54 , pp. 3231
- Pridgen, L.N.¹ Prol, J.² Alexander, B.³ Gillyard, L.⁴

29
- 0001001958
- 1c: L. F. Tietze, C. Schneider, A. Grote, Chem. Eur. J. 1996, 2, 139;
- (1996) Chem. Eur. J. , vol.2 , pp. 139
- Tietze, L.F.¹ Schneider, C.² Grote, A.³

30
- 0028297594
- 1d: T. Akiba, O. Tamura, M. Hashimoto, Y. Kobayashi, T. Katoh, K. Nakatani, M. Kamada, I. Hayakawa, S. Terashima, Tetrahedron 1994, 50, 3905.
- (1994) Tetrahedron , vol.50 , pp. 3905
- Akiba, T.¹ Tamura, O.² Hashimoto, M.³ Kobayashi, Y.⁴ Katoh, T.⁵ Nakatani, K.⁶ Kamada, M.⁷ Hayakawa, I.⁸ Terashima, S.⁹

31
- 0001469497
- 15. W. Sankhavasi, M. Yamamoto, S. Kohmoto, K. Yamada, Bull. Chem. Soc. Jpn. 1991, 64, 1425.
- (1991) Bull. Chem. Soc. Jpn. , vol.64 , pp. 1425
- Sankhavasi, W.¹ Yamamoto, M.² Kohmoto, S.³ Yamada, K.⁴

32
- 0001675785
- 16. L. Grehn, U. Ragnarsson, Angew. Chem. 1985, 97, 519; Angew. Chem. Int. Ed. Engl. 1985, 24, 510; M. Wakselman in Encyclopedia of Reagents for Organic Synthesis, Ed.: L. A. Paquette, Wiley, Chichester, 1995, p. 1602; U. Ragnarsson, L. Grehn, Acc. Chem. Res. 1998, 31, 494, et loc. cit.
- (1985) Angew. Chem. , vol.97 , pp. 519
- Grehn, L.¹ Ragnarsson, U.²

33
- 84985633562
- 16. L. Grehn, U. Ragnarsson, Angew. Chem. 1985, 97, 519; Angew. Chem. Int. Ed. Engl. 1985, 24, 510; M. Wakselman in Encyclopedia of Reagents for Organic Synthesis, Ed.: L. A. Paquette, Wiley, Chichester, 1995, p. 1602; U. Ragnarsson, L. Grehn, Acc. Chem. Res. 1998, 31, 494, et loc. cit.
- (1985) Angew. Chem. Int. Ed. Engl. , vol.24 , pp. 510

34
- 0001017063
- Ed.: L. A. Paquette, Wiley, Chichester
- 16. L. Grehn, U. Ragnarsson, Angew. Chem. 1985, 97, 519; Angew. Chem. Int. Ed. Engl. 1985, 24, 510; M. Wakselman in Encyclopedia of Reagents for Organic Synthesis, Ed.: L. A. Paquette, Wiley, Chichester, 1995, p. 1602; U. Ragnarsson, L. Grehn, Acc. Chem. Res. 1998, 31, 494, et loc. cit.
- (1995) Encyclopedia of Reagents for Organic Synthesis , pp. 1602
- Wakselman, M.¹

35
- 0000784289
- et loc. cit
- 16. L. Grehn, U. Ragnarsson, Angew. Chem. 1985, 97, 519; Angew. Chem. Int. Ed. Engl. 1985, 24, 510; M. Wakselman in Encyclopedia of Reagents for Organic Synthesis, Ed.: L. A. Paquette, Wiley, Chichester, 1995, p. 1602; U. Ragnarsson, L. Grehn, Acc. Chem. Res. 1998, 31, 494, et loc. cit.
- (1998) Acc. Chem. Res. , vol.31 , pp. 494
- Ragnarsson, U.¹ Grehn, L.²

36
- 0010325607
- note
- 5: C 61.07, H 6.63, N 8.38; found: C 61.07, H 6.70, N 8.29.

37
- 0029849537
- 18. D. J. Ager, D. R. Allen, D. R. Schaad, Synthesis 1996, 1283.
- (1996) Synthesis , pp. 1283
- Ager, D.J.¹ Allen, D.R.² Schaad, D.R.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.