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Tetrahedron Letters

Volumn 19, Issue 34, 1978, Pages 3129-3132

Syntheses via isoxazolines II. Novel 4-substituted 2-isoxazolines byendo-deprotonation/alkylation

(2) Jager V a Schwab, W a

a JUSTUS LIEBIG UNIVERSITY (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001397747 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(01)94962-7 Document Type: Article

Times cited : (55)

References (26)

1
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- Lednicer¹

2
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- J. Wiley a. Sons, New York-London-Sydney-Toronto
- (1974) Heterocycles in Organic Synthesis
- Meyers¹

3
- 0017089468
- cf. recent examples of isoxazole-mediated syntheses of corphin and corrin systems:
- (1976) Journal of the American Chemical Society , vol.98 , pp. 6313
- Stevensetal¹

4
- 0017086010
- and references cited
- (1976) Journal of the American Chemical Society , vol.98 , pp. 6317
- Stevensetal¹

5
- 0012824710
- For reviews and leading references see, A. Weissberger, Interscience Publ, New York-London
- (1962) The Chemistry of Heterocyclic Compounds , vol.17 , pp. 95
- Quilico¹

6
- 0004254523
- Springer-Verlag, Berlin-Heidelberg-New York
- (1971) The Nitrile Oxides , pp. 96
- Grundmann¹ Grünanger²

7
- 33847799231
- (1976) J. Org. Chem. , vol.41 , pp. 403
- Huisgen¹

8
- 84910292576
- V. Jäger, V. Buß and W. Schwab, following paper; cp. also literature cited therein.

9
- 84910314287
- Some other useful conversions in this context are: aziridine formation from 3.4-diphenyl-2-isoxazolines [K. Kotera, Y. Takano, A. Matsuura and K. Kitahonoki, Tetrahedron 26, 539(1970)]; conversion to isoxazoles which, in turn, are widely-used “vehicles”.

10
- 0042223241
- Cp. related dianions of oximes:
- (1969) J. Amer. Chem. Soc. , vol.91 , pp. 676
- Henoch¹ Hampton² Hauser³

11
- 0001424311
- (1970) J. Org. Chem. , vol.35 , pp. 1806
- Beam¹ Dyer² Schwarz³ Hauser⁴

12
- 0017192635
- (1976) J. Pharm. Sci. , vol.65 , pp. 1408
- Beam¹

13
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- (1976) J. Org. Chem. , vol.41 , pp. 439
- Kofron¹ Yeh²

14
- 0002876522
- (1976) Tetrahedron Letters , pp. 1439
- Jung¹ Blair² Lowe³

15
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- (1976) Tetrahedron Letters , pp. 4431
- Lyle¹

16
- 0003046310
- anions of acyclic oxime ethers:
- (1975) Tetrahedron Letters , pp. 3889
- Spencer¹ Leong²

17
- 37049101887
- (1976) Journal of the Chemical Society, Chemical Communications , pp. 674
- Fraser¹ Dhawan²

18
- 84910298994
- 4-Endo-anions here correspond to syn-, 3′ -exo-anions of 2-isoxazolines to anti-anions of acyclic analogues such as oximes or oxime ethers.

19
- 0004860602
- Nitrile oxide addition to mono-substituted alkenes exclusively furnishes 5-alkyl derivatives. We are aware of only two mono-cyclic 4-substituted 2-isoxazolines that have been obtained in low yield from enone precursors:
- (1970) Tetrahedron Letters , pp. 2993
- MacConaill¹ Scott²

20
- 0010169135
- 6 Annulated 3.4-disubstitutedisoxazolines have been obtained by intramolecular 1.3-dipolar cycloaddition:
- (1975) Chim. Ind. (Milano) , vol.57 , pp. 16
- Fusco¹ Garanti² Zecchi³

21
- 0001201955
- (1975) J. Org. Chem. , vol.40 , pp. 2403
- Garanti¹ Sala² Zecchi³

22
- 80054730956
- (1977) Angewandte Chemie , vol.89 , pp. 253
- Jäger¹ Günther²

23
- 84980170799
- (1977) Angewandte Chemie International Edition in English , vol.16 , pp. 246
- Jäger¹ Günther²

24
- 84910284528
- Equilibration of cis/trans isomers by proton or deuterium transfer during work-up is unlikely: 7a in this case should consist of a~ 1:1 cis/trans-mixture; further, in a preliminary experiment to deprotonate/deuterate cis-4.5-dimethyl-3-phenyl-2-isoxazoline, the non-deuterated part of the product contained only educt and none of the trans isomer.

25
- 84910239273
- This work was supported by the Deutsche Forschungsgemeinschaft.

26
- 84910284804
- This and the following paper are dedicated to Prof. F. Kröhnke on the occasion of his 75th birthday.

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