SCOPUS 정보 검색 플랫폼

European Journal of Organic Chemistry

Volumn , Issue 2, 2009, Pages 199-203

Highly regio- and diastereoselective oxazol-5-one addition to nitrostyrenes

(6) Balaguer, Andrea Nekane a Companyó, Xavier a Calvet, Teresa a Font Bardía, Mercé a Moyano, Albert a Rios, Ramon a

a UNIVERSITY OF BARCELONA (Spain)

Author keywords

Diastereoselective catalysis; Heterocycles; Michael addition; N,O aminals; Nitrostyrenes; Organocatalysis

Indexed keywords

EID: 58649093531 PISSN: 1434193X EISSN: 10990690 Source Type: Journal
DOI: 10.1002/ejoc.200801005 Document Type: Article

Times cited : (49)

References (34)

1
- 0001521888
- For reviews in this topic see: a
- For reviews in this topic see: a) K. Fuji, Chem. Rev. 1993, 93, 2037-2066;
- (1993) Chem. Rev , vol.93 , pp. 2037-2066
- Fuji, K.¹

2
- 0000261234
- b) E. J. Corey, A. Guzmán-Pérez, Angew. Chem. Int. Ed. 1998, 37, 389-401;
- (1998) Angew. Chem. Int. Ed , vol.37 , pp. 389-401
- Corey, E.J.¹ Guzmán-Pérez, A.²

3
- 0035905575
- c) J. Christoffers, A. Mann, Angew. Chem. Int. Ed. 2001, 40, 4591-4597;
- (2001) Angew. Chem. Int. Ed , vol.40 , pp. 4591-4597
- Christoffers, J.¹ Mann, A.²

4
- 0037541354
- d) J. Christoffers, A. Baro, Angew. Chem. Int. Ed. 2003, 42, 1688-1690.
- (2003) Angew. Chem. Int. Ed , vol.42 , pp. 1688-1690
- Christoffers, J.¹ Baro, A.²

5
- 58649098820
- Examples of oxazol-5-one reactions: a J. Liang, J. C. Ruble, G. C. Fu, J. Org. Chem. 1998, 63, 3154-3155;
- Examples of oxazol-5-one reactions: a) J. Liang, J. C. Ruble, G. C. Fu, J. Org. Chem. 1998, 63, 3154-3155;

6
- 13444270903
- b) A. Berkessel, F. Cleemann, S. Mukherkee, T. N. Mueller, J. Lex, Angew. Chem. Int. Ed. 2005, 44, 807-811;
- (2005) Angew. Chem. Int. Ed , vol.44 , pp. 807-811
- Berkessel, A.¹ Cleemann, F.² Mukherkee, S.³ Mueller, T.N.⁴ Lex, J.⁵

7
- 17444385209
- c) A. Berkessel, S. Mukherkee, F. Cleemann, T. N. Mueller, J. Lex, Chem. Commun. 2005, 14, 1898-1900;
- (2005) Chem. Commun , vol.14 , pp. 1898-1900
- Berkessel, A.¹ Mukherkee, S.² Cleemann, F.³ Mueller, T.N.⁴ Lex, J.⁵

8
- 33750970292
- d) A. Berkessel, S. Mukherkee, T. N. Mueller, F. Cleemann, K. Roland, M. Brandenburg, J. M. Neudoerfl, J. Lex, Org. Biomol. Chem. 2006, 4, 4319-4330;
- (2006) Org. Biomol. Chem , vol.4 , pp. 4319-4330
- Berkessel, A.¹ Mukherkee, S.² Mueller, T.N.³ Cleemann, F.⁴ Roland, K.⁵ Brandenburg, M.⁶ Neudoerfl, J.M.⁷ Lex, J.⁸

9
- 0033601122
- e) B. M. Trost, X. Ariza, J. Am. Chem. Soc. 1999, 121, 10727-10737;
- (1999) J. Am. Chem. Soc , vol.121 , pp. 10727-10737
- Trost, B.M.¹ Ariza, X.²

10
- 0037178119
- f) B. M. Trost, K. Dogra, J. Am. Chem. Soc. 2002, 124, 7256-7257;
- (2002) J. Am. Chem. Soc , vol.124 , pp. 7256-7257
- Trost, B.M.¹ Dogra, K.²

11
- 0347613016
- g) B. M. Trost, C. Jakel, B. Plietker, J. Am. Chem. Soc. 2003, 125, 4438-4439.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 4438-4439
- Trost, B.M.¹ Jakel, C.² Plietker, B.³

12
- 84981886798
- W. Steglich, P. Grüber, G. Höfle, W. König, Angew. Chem. Int. Ed. Engl. 1971, 10, 653-655.
- (1971) Angew. Chem. Int. Ed. Engl , vol.10 , pp. 653-655
- Steglich, W.¹ Grüber, P.² Höfle, G.³ König, W.⁴

13
- 0006913662
- a) W. Steglich, G. Höfle, Chem. Ber. 1969, 102, 883-898;
- (1969) Chem. Ber , vol.102 , pp. 883-898
- Steglich, W.¹ Höfle, G.²

14
- 84980915455
- b) W. Steglich, G. Höfle, Chem. Ber. 1969, 102, 1129-1147;
- (1969) Chem. Ber , vol.102 , pp. 1129-1147
- Steglich, W.¹ Höfle, G.²

15
- 84981760409
- c) W. Steglich, G. Höfle, Chem. Ber. 1969, 102, 899-903;
- (1969) Chem. Ber , vol.102 , pp. 899-903
- Steglich, W.¹ Höfle, G.²

16
- 84981868071
- d) W. Reid, H. Mengler, Justus Liebigs Ann. Chem. 1964, 678, 113-116.
- (1964) Justus Liebigs Ann. Chem , vol.678 , pp. 113-116
- Reid, W.¹ Mengler, H.²

17
- 51749120761
- S. Cabrera, E. Reyes, J. Alemán, A. Mielli, S. Kobbelgaard, K. A. Jorgensen, J. Am. Chem. Soc. 2008, 130, 12031-12037.
- (2008) J. Am. Chem. Soc , vol.130 , pp. 12031-12037
- Cabrera, S.¹ Reyes, E.² Alemán, J.³ Mielli, A.⁴ Kobbelgaard, S.⁵ Jorgensen, K.A.⁶

18
- 34250613134
- For recent reviews of asymmetric organocatalytic 1,4-conjugated additions, see: a
- For recent reviews of asymmetric organocatalytic 1,4-conjugated additions, see: a) S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701-1716;
- (2007) Eur. J. Org. Chem , pp. 1701-1716
- Tsogoeva, S.B.¹

19
- 34547198987
- b) J. L. Vicario, D. Badía, L. Carrillo, Synthesis 2007, 2065-2092.
- (2007) Synthesis , pp. 2065-2092
- Vicario, J.L.¹ Badía, D.² Carrillo, L.³

20
- 0035852116
- a) A. B. Smith III, I. G. Safanov, R. M. Corbett, J. Am. Chem. Soc. 2001, 123, 12426-12427;
- (2001) J. Am. Chem. Soc , vol.123 , pp. 12426-12427
- Smith III, A.B.¹ Safanov, I.G.² Corbett, R.M.³

21
- 0037149691
- b) D. M. Troast, J. A. Porco, Org. Lett. 2002, 4, 991-994.
- (2002) Org. Lett , vol.4 , pp. 991-994
- Troast, D.M.¹ Porco, J.A.²

22
- 19744376535
- J.-H. Sohn, N. Waizumi, M. Z. Zhong, V. H. Rawal, J. Am. Chem. Soc. 2005, 127, 7290-7291.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 7290-7291
- Sohn, J.-H.¹ Waizumi, N.² Zhong, M.Z.³ Rawal, V.H.⁴

23
- 34548299144
- J. C. Jewett, V. H. Rawal, Angew. Chem. Int. Ed. 2007, 46, 6502-6504.
- (2007) Angew. Chem. Int. Ed , vol.46 , pp. 6502-6504
- Jewett, J.C.¹ Rawal, V.H.²

24
- 3042706094
- a) R. H. Cichewicz, F. A. Valeriote, P. Crews, Org. Lett. 2004, 6, 1951-1954;
- (2004) Org. Lett , vol.6 , pp. 1951-1954
- Cichewicz, R.H.¹ Valeriote, F.A.² Crews, P.³

25
- 23844506416
- b) X. Jiang, J. Garcia-Fontanet, J. K. DeBrabander, J. Am. Chem. Soc. 2005, 127, 11254-11255.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 11254-11255
- Jiang, X.¹ Garcia-Fontanet, J.² DeBrabander, J.K.³

26
- 33846589318
- X. Jiang, N. Williams, J. K. DeBrabander, Org. Lett. 2007, 9, 227-230.
- (2007) Org. Lett , vol.9 , pp. 227-230
- Jiang, X.¹ Williams, N.² DeBrabander, J.K.³

27
- 51949105698
- G. Li, F. R. Foronczek, J. C. Antilla, J. Am. Chem. Soc. 2008, 130, 12216-12217.
- (2008) J. Am. Chem. Soc , vol.130 , pp. 12216-12217
- Li, G.¹ Foronczek, F.R.² Antilla, J.C.³

28
- 19644380904
- For the synthesis of oxazol-5-ones see: a
- For the synthesis of oxazol-5-ones see: a) A. Llinás, N. Ahmed, M. Cordaro, A. P. Laws, J. M. Frère, M. Delmarcelle, N. R. Silvaggi, J. A. Kelly, M. I. Page, Biochemistry 2005, 44, 7738-7746;
- (2005) Biochemistry , vol.44 , pp. 7738-7746
- Llinás, A.¹ Ahmed, N.² Cordaro, M.³ Laws, A.P.⁴ Frère, J.M.⁵ Delmarcelle, M.⁶ Silvaggi, N.R.⁷ Kelly, J.A.⁸ Page, M.I.⁹

29
- 34447285219
- b) C. O. Dalaigh, S. A. Corr, Y. Gun'ko, S. J. Connon, Angew. Chem. Int. Ed. 2007, 46, 4329-4332.
- (2007) Angew. Chem. Int. Ed , vol.46 , pp. 4329-4332
- Dalaigh, C.O.¹ Corr, S.A.² Gun'ko, Y.³ Connon, S.J.⁴

30
- 58649092216
- In an initial experiment, -cinchonidine catalyzed the organocatalytic addition of oxazol-5-one 2a to nitrostyrene 1a in 94% yield; diastereoselective ratio 10:1, ee, 30
- In an initial experiment (-)-cinchonidine catalyzed the organocatalytic addition of oxazol-5-one 2a to nitrostyrene 1a in 94% yield; diastereoselective ratio 10:1, ee = 30%.

31
- 84868889443
- X-ray difraction of 4b: A prismatic crystal (0.1 x 0.1 x 0.2 mm) was selected and mounted on a MAR345 diffractometer with an image plate detector. Unit-cell parameters were determined from 209 reflections (3 < θ < 31°) and refined by least-squares method. Intensities were collected with graphite-monochromatized Mo-Kα radiation. 12257 reflections were measured in the range 2.59° ≤ θ ≤30.29°. 4033 of which were non-equivalent by symmetry [R int(on I, 0.046, 3412 reflections were assumed as observed applying the condition I>2σ(I, Lorentz polarization but no absorption corrections were made. The structure was solved by Direct methods, using SHELXS computer program G. M. Sheldrick, A program for automatic solution of crystal structure, University of Göttingen, Germany, 1990
- int(on I) = 0.046]. 3412 reflections were assumed as observed applying the condition I>2σ(I). Lorentz polarization but no absorption corrections were made. The structure was solved by Direct methods, using SHELXS computer program (G. M. Sheldrick, A program for automatic solution of crystal structure, University of Göttingen, Germany, 1990)

32
- 84868872435
- and refined by full-matrix least-squares method with SHELX97 computer program (G. M. Sheldrick, A program for crystal structure refinement, University of Göttingen, Germany, 1997), using 12257 reflections, (very negative intensities were not assumed).
- and refined by full-matrix least-squares method with SHELX97 computer program (G. M. Sheldrick, A program for crystal structure refinement, University of Göttingen, Germany, 1997), using 12257 reflections, (very negative intensities were not assumed).

33
- 84868871257
- The function minimized was Σw∥Fo| 2, Fc|2|2, where w, σ2(I, 0.0857P)2, 0.0102P]-1, and P, Fo|2, 2 |Fc|2)/3, f, f′ and f″ were taken from International Tables of X-ray Crystallography (International Tables of X-ray Crystallography, Kynoch Press, 1974, IV, pp. 99-100 and 149, All H atoms were computed and refined, using a riding model, with an isotropic temperature factor equal to 1.2 time the equivalent temperature factor of the atom which are linked. The final R(on F) factor was 0.056, wR(on |F|2) was 0.063 and goodness of fit was 1.139 for all observed reflections. The number of refined parameters was 219; max. shift/esd, 0.00, mean shift/esd, 0.00; max. and min. peaks in f
- -3, respectively. CCDC-705916 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.

34
- 0345324148
- For an alternative synthesis, starting with cyanohydrins
- For an alternative synthesis, starting with cyanohydrins: S. A. Ferrino, L. A. Maldonado, Synth. Commun. 1980, 10, 717-723.
- (1980) Synth. Commun , vol.10 , pp. 717-723
- Ferrino, S.A.¹ Maldonado, L.A.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.