SCOPUS 정보 검색 플랫폼

Volumn 33, Issue 51, 1992, Pages 7889-7892

Lewis acid-catalyzed nitrone cycloadditions to bidentate and tridentate α,β-unsaturated ketones. High rate acceleration, absolutely endo-selective and regioselective reactions

(3) Kanemasa, Shuji a Uemura, Takashi a Wada, Eiji a

a KYUSHU UNIVERSITY (Japan)

Author keywords

Bidentate and tridentate enone; Dipolar cycloaddition; Lewis acid; Nitrone; Regiocontrol; Stereocontrol

Indexed keywords

ISOXAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0027080183 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)74770-8 Document Type: Article

Times cited : (74)

References (17)

1
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- Tufariello¹

2
- 0002294391
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- Confalone¹ Huie²

3
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- S. Patai, Z. Rappoport, John Wiley & Sons, New York
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- Breuer¹ Aurich² Nielsen³

4
- 0003667457
- American Chemical Society, Washington
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- Desimoni¹ Tacconi² Barco³ Pollini⁴

5
- 0002899589
- Intramolecular 1,3-Dipolar Cycloaddition Chemistry
- D.P. Curran, JAI Press, Greenwich
- (1990) Advances in Cycloaddition , vol.2 , pp. 1-89
- Padwa¹ Schoffstall²

6
- 0007954504
- Asymmetric Diels-Alder Reactions
- T. Hudlicky, JAI Press, Greenwich
- (1989) Organic Synthesis - Theory and Applications , vol.1 , pp. 1-101
- Taschner¹

7
- 0003523008
- Pergamon Press, Oxford
- (1990) Cycloaddition Reactions in Organic Synthesis , pp. 1-208
- Carruthers¹

8
- 0000804098
- Metal-assisted dipolar cycloadditions:
- (1988) Tetrahedron , vol.44 , pp. 557-570
- Barr¹ Grigg² Gunaratune³ Kemp⁴ McMeekin⁵ Sridharan⁶

9
- 33845279732
- (1988) J. Org. Chem. , vol.53 , pp. 1384-1391
- Tsuge¹ Kanemasa² Yoshioka³

10
- 0026003250
- (1991) Tetrahedron Lett. , vol.32 , pp. 5817-5820
- Allway¹ Grigg²

11
- 84914289416
- The dipole complex as a major contributor deactivates cycloadditions, while the minor dipolarophile complex activates. Control of this equilibrium in favor of the dipolarophile complex is a point.

12
- 84914289415
- Enones 2 and 3 were prepared by phosphorylmethylation of ethyl benzyloxyacetate and ethyl (2-phenyl-thioethyl) acetate, respectively, followed by Horner-Emmons olefination with acetaldehyde. Enone 4 was prepared by a sequence of aldol reaction of the dianion of diethyl 2-oxopropylphosphonate, O-mesylation, and elimination.

13
- 84914289414
- All isolable products reported herein were fully characterized on the basis of spectral data.

14
- 84914289413
- 2O, and PhCH [[Truncated]]

15
- 84914289412
- 2 (one equivalent) with a 1:1 mixture of 2 and 5a only causes the lowfield shifts of protons of 5a, indicating the catalyst is mostly incorporated in 5a.

16
- 84914289411
- 11

17
- 37049101308
- Dynamic stereochemistry of imines and derivatives. Part 11. Synthesis and stereochemistry of (E)- and (Z)-nitrones
- (1977) Journal of the Chemical Society, Perkin Transactions 1 , pp. 254-259
- Bjorgo¹ Boyd² Neil³ Jennings⁴

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