SCOPUS 정보 검색 플랫폼

Volumn , Issue 4, 2004, Pages 776-782

Fully stereoselective nucleophilic addition to a novel chiral pyrroline N-oxide: Total syntheses of (2S,3R)-3-hydroxy-3-methylproline and its (2R)-epimer

(5) Merino, Pedro a Revuelta, Julia a Tejero, Tomas a Cicchi, Stefano b Goti, Andrea b

a UNIVERSITY OF ZARAGOZA (Spain)

b UNIVERSITY OF FLORENCE (Italy)

Author keywords

Amino acids; Nitrones; Nucleophilic additions; Proline; Pyrrolidines

Indexed keywords

3 HYDROXY 3 METHYLPROLINE; ACID; CITRAMALIC ACID; LITHIUM DERIVATIVE; METHYL GROUP; NITRONE; OXIDE; PROLINE DERIVATIVE; PYRROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHIRALITY; EPIMER; OXIDATION REDUCTION REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 4544257545 PISSN: 1434193X EISSN: None Source Type: Journal
DOI: 10.1002/ejoc.200300608 Document Type: Article

Times cited : (54)

References (35)

1
- 0037605171
- C. Najera, M. Yus, Tetrahedron: Asymmetry 1999, 10, 2245-2303.
- (1999) Tetrahedron: Asymmetry , vol.10 , pp. 2245-2303
- Najera, C.¹ Yus, M.²

2
- 0030605059
- P. Remuzon, Tetrahedron 1996, 52, 13803-13835.
- (1996) Tetrahedron , vol.52 , pp. 13803-13835
- Remuzon, P.¹

3
- 0037185422
- H. Watanabe, M. Okue, H. Kobayashi, T. Kitahara, Tetrahedron Lett. 2002, 43, 861-864.
- (2002) Tetrahedron Lett. , vol.43 , pp. 861-864
- Watanabe, H.¹ Okue, M.² Kobayashi, H.³ Kitahara, T.⁴

4
- 0037450463
- A. L. L. Garcia, C. R. D. Correia, Tetrahedron Lett. 2003, 44, 1553-1557.
- (2003) Tetrahedron Lett. , vol.44 , pp. 1553-1557
- Garcia, A.L.L.¹ Correia, C.R.D.²

5
- 0032510429
- K. Umezawa, K. Nakazawa, T. Uemura, Y. Ikeda, S. Kondo, H. Naganawa, N. Kinoshita, H. Hashizume, M. Hamada, T. Takeuchi, S. Ohba, Tetrahedron Lett. 1998, 39, 1389-1392.
- (1998) Tetrahedron Lett. , vol.39 , pp. 1389-1392
- Umezawa, K.¹ Nakazawa, K.² Uemura, T.³ Ikeda, Y.⁴ Kondo, S.⁵ Naganawa, H.⁶ Kinoshita, N.⁷ Hashizume, H.⁸ Hamada, M.⁹ Takeuchi, T.¹⁰ Ohba, S.¹¹

6
- 0033617279
- K. Umezawa, K. Nakazawa, Y. Ikeda, H. Naganawa, S. Kondo, J. Org. Chem. 1999, 64, 3034-3038.
- (1999) J. Org. Chem. , vol.64 , pp. 3034-3038
- Umezawa, K.¹ Nakazawa, K.² Ikeda, Y.³ Naganawa, H.⁴ Kondo, S.⁵

7
- 0032879494
- K. Umezawa, K. Nakazawa, Y. Uchihata, M. Otsuka, Adv. Enzyme Regul. 1999, 39, 145-156.
- (1999) Adv. Enzyme Regul. , vol.39 , pp. 145-156
- Umezawa, K.¹ Nakazawa, K.² Uchihata, Y.³ Otsuka, M.⁴

8
- 0035974397
- Y. Noguchi, H. Uchiro, T. Yamada, S. Kobayashi, Tetrahedron Lett. 2001, 42, 5253-5256.
- (2001) Tetrahedron Lett. , vol.42 , pp. 5253-5256
- Noguchi, Y.¹ Uchiro, H.² Yamada, T.³ Kobayashi, S.⁴

9
- 0037189184
- K. Makino, A. Kondoh, Y. Hamada, Tetrahedron Lett. 2002, 43, 4695-4698.
- (2002) Tetrahedron Lett. , vol.43 , pp. 4695-4698
- Makino, K.¹ Kondoh, A.² Hamada, Y.³

10
- 0037039910
- D. G. Qin, H.-Y. Zha, Z.-J. Yao, J. Org. Chem. 2002, 67, 1038-1040.
- (2002) J. Org. Chem. , vol.67 , pp. 1038-1040
- Qin, D.G.¹ Zha, H.-Y.² Yao, Z.-J.³

11
- 4544268687
- J.-W. Sen, D.-G. Qin, H.-W. Zhang, Z.-J. Yao, J. Org. Chem. 2003, 67, 7479-7484.
- (2003) J. Org. Chem. , vol.67 , pp. 7479-7484
- Sen, J.-W.¹ Qin, D.-G.² Zhang, H.-W.³ Yao, Z.-J.⁴

12
- 4544352310
- (in press) and references cited therein
- P. Merino, in Targets in Heterocyclic Chemistry 2003, (in press) and references cited therein.
- (2003) Targets in Heterocyclic Chemistry
- Merino, P.¹

13
- 0037423128
- P. Merino, T. Tejero, J. Revuelta, P. Romero, S. Cicchi, V. Mannucci, A. Brandi, A. Goti, Tetrahedron: Asymmetry 2003, 14, 367-379.
- (2003) Tetrahedron: Asymmetry , vol.14 , pp. 367-379
- Merino, P.¹ Tejero, T.² Revuelta, J.³ Romero, P.⁴ Cicchi, S.⁵ Mannucci, V.⁶ Brandi, A.⁷ Goti, A.⁸

14
- 0030969628
- A. Goti, S. Cicchi, V. Fedi, L. Nannelli, A. Brandi, J. Org. Chem. 1997, 62, 3119-3125.
- (1997) J. Org. Chem. , vol.62 , pp. 3119-3125
- Goti, A.¹ Cicchi, S.² Fedi, V.³ Nannelli, L.⁴ Brandi, A.⁵

15
- 0029162529
- S. Cicchi, A. Goti, A. Brandi, J. Org. Chem. 1995, 60, 4743-4748.
- (1995) J. Org. Chem. , vol.60 , pp. 4743-4748
- Cicchi, S.¹ Goti, A.² Brandi, A.³

16
- 0033757646
- A. Goti, S. Cicchi, F. Cardona, V. Fedi, A. Brandi, Eur. J. Org. Chem. 2000, 3633-3645.
- (2000) Eur. J. Org. Chem. , pp. 3633-3645
- Goti, A.¹ Cicchi, S.² Cardona, F.³ Fedi, V.⁴ Brandi, A.⁵

17
- 0033515793
- A. Goti, M. Cacciarini, F. Cardona, A. Brandi, Tetrahedron Lett. 1999, 40, 2853-2856.
- (1999) Tetrahedron Lett. , vol.40 , pp. 2853-2856
- Goti, A.¹ Cacciarini, M.² Cardona, F.³ Brandi, A.⁴

18
- 0000028432
- S. Cicchi, I. Höld, A. Brandi, J. Org. Chem. 1993, 58, 5274-5275.
- (1993) J. Org. Chem. , vol.58 , pp. 5274-5275
- Cicchi, S.¹ Höld, I.² Brandi, A.³

19
- 0037040659
- S. Cicchi, M. Corsi, A. Brandi, A. Goti, J. Org. Chem. 2002, 67, 1678-1681.
- (2002) J. Org. Chem. , vol.67 , pp. 1678-1681
- Cicchi, S.¹ Corsi, M.² Brandi, A.³ Goti, A.⁴

20
- 0037430434
- F. Cardona, E. Faggi, F. Liguori, M. Cacciarini, A. Goti, Tetrahedron Lett. 2003, 44, 2315-2318.
- (2003) Tetrahedron Lett. , vol.44 , pp. 2315-2318
- Cardona, F.¹ Faggi, E.² Liguori, F.³ Cacciarini, M.⁴ Goti, A.⁵

21
- 0034619615
- F. J. Duff, V. Vivien, R. H. Wightman, Chem. Commun. 2000, 2127-2128.
- (2000) Chem. Commun. , pp. 2127-2128
- Duff, F.J.¹ Vivien, V.² Wightman, R.H.³

22
- 0028871717
- P. de March, M. Figueredo, J. Font, T. Gallagher, S. Milán, Chem. Commun. 1995, 2097-2098.
- (1995) Chem. Commun. , pp. 2097-2098
- De March, P.¹ Figueredo, M.² Font, J.³ Gallagher, T.⁴ Milán, S.⁵

23
- 0036331107
- O. Tamura, A. Toyao, H. Ishibashi, Synlett 2002, 1344-1346.
- (2002) Synlett , pp. 1344-1346
- Tamura, O.¹ Toyao, A.² Ishibashi, H.³

24
- 0030513666
- T. Ishikawa, Y. Tajima, M. Fukui, S. Saito, Angew. Chem. Int. Ed. Engl. 1996, 35, 1863-1864.
- (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 1863-1864
- Ishikawa, T.¹ Tajima, Y.² Fukui, M.³ Saito, S.⁴

25
- 0035840368
- S. Cicchi, M. Marradi, A. Goti, A. Brandi, Tetrahedron Lett. 2001, 42, 6503-6505.
- (2001) Tetrahedron Lett. , vol.42 , pp. 6503-6505
- Cicchi, S.¹ Marradi, M.² Goti, A.³ Brandi, A.⁴

26
- 0037074092
- For a recent example from our laboratories, see: P. Merino, S. Franco, F. L. Merchan, J. Revuelta, T. Tejero, Tetrahedron Lett. 2002, 43, 459-462.
- (2002) Tetrahedron Lett. , vol.43 , pp. 459-462
- Merino, P.¹ Franco, S.² Merchan, F.L.³ Revuelta, J.⁴ Tejero, T.⁵

27
- 0007234403
- (Ed.: S. G. Pandalai), Transworld Research Network, Trivandum, India
- For a review, see: P. Merino, S. Franco, F. L. Merchan, T. Tejero, Oxidations of Furan Rings in Organic Synthesis: Expanding Synthetic Utility of Aromatic Heterocycles. In Recent Research Development in Synthetic Organic Chemistry (Ed.: S. G. Pandalai), Transworld Research Network, Trivandum, India, 2000, vol. 3. pp. 65-74.
- (2000) Oxidations of Furan Rings in Organic Synthesis: Expanding Synthetic Utility of Aromatic Heterocycles. In Recent Research Development in Synthetic Organic Chemistry , vol.3 , pp. 65-74
- Merino, P.¹ Franco, S.² Merchan, F.L.³ Tejero, T.⁴

28
- 0034629360
- For a recent example carried out in our laboratory, see: P. Merino, S. Anoro, S. Franco, F. L. Merchan, T. Tejero, V. Tunon, J. Org. Chem. 2000, 65, 1590-1596.
- (2000) J. Org. Chem. , vol.65 , pp. 1590-1596
- Merino, P.¹ Anoro, S.² Franco, S.³ Merchan, F.L.⁴ Tejero, T.⁵ Tunon, V.⁶

29
- 0028585804
- A. Dondoni, F. Junquera, F. L. Merchan, P. Merino, T. Tejero, Synthesis 1994, 1450-1456.
- (1994) Synthesis , pp. 1450-1456
- Dondoni, A.¹ Junquera, F.² Merchan, F.L.³ Merino, P.⁴ Tejero, T.⁵

30
- 0000997345
- A. Dondoni, F. Junquera, F. L. Merchan, P. Merino, M.-C. Scherrmann, T. Tejero, J. Org. Chem. 1997, 62, 5484-5496.
- (1997) J. Org. Chem. , vol.62 , pp. 5484-5496
- Dondoni, A.¹ Junquera, F.² Merchan, F.L.³ Merino, P.⁴ Scherrmann, M.-C.⁵ Tejero, T.⁶

31
- 0141674892
- S. Cicchi, M. Bonanni, F. Cardona, J. Revuelta, A. Goti, Org. Lett. 2003, 5, 1773-1776.
- (2003) Org. Lett. , vol.5 , pp. 1773-1776
- Cicchi, S.¹ Bonanni, M.² Cardona, F.³ Revuelta, J.⁴ Goti, A.⁵

32
- 0034112410
- Lewis acids are able to control the stereochemical outcome of nucleophilic additions to acyclic α-alkoxy nitrones. For an account, see: P. Merino, S. Franco, F. L. Merchan, T. Tejero, Synlett 2000, 442-454.
- (2000) Synlett , pp. 442-454
- Merino, P.¹ Franco, S.² Merchan, F.L.³ Tejero, T.⁴

33
- 49949128203
- M. Chérest, H. Felkin, N. Prudent, Tetrahedron Lett. 1968, 2199-2204.
- (1968) Tetrahedron Lett. , pp. 2199-2204
- Chérest, M.¹ Felkin, H.² Prudent, N.³

34
- 0002451214
- N. T. Anh, O. Eisenstein, Nouv. J. Chimie 1977, 1, 61-70.
- (1977) Nouv. J. Chimie , vol.1 , pp. 61-70
- Anh, N.T.¹ Eisenstein, O.²

35
- 33845281918
- E. P. Lodge, C. H. Heathcock, J. Am. Chem. Soc. 1987, 109, 2819-2820.
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 2819-2820
- Lodge, E.P.¹ Heathcock, C.H.²

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