Stereoselective nucleophilic substitution reactions of 2-methoxy- and 2,3-diacyloxypiperidines catalyzed by scandium triflate

Synlett

Volumn , Issue 7, 2000, Pages 989-990

  Okitsu, Osamu ^a   Suzuki, Ritsu ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Aza sugar; Piperidine; Sandium triflate; Stereoselective; Substitution reaction

Indexed keywords

PIPERIDINE DERIVATIVE; SCANDIUM;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0033944318     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (20)

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2. (b) Kobayashi, S.; Ueno, M.; Suzuki, R.; Ishitani, H. Tetrahedron Lett. 1999, 40, 2175.
3. For racemic synthesis of febrifugine and derivatives, (a) Takeuchi, Y.; Tokuda, S.; Takagi, T.; Koike, M.; Abe, H.; Harayama, T.; Shibata, Y.; Kim, H.; Wataya, Y. Heterocyles 1999, 51, 1869.
4. (b) Takeuchi, Y.; Hattori, M.; Abe, H.; Harayama, T. Synthesis 1999, 1814.
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9. For recent reviews of C-glycosylation, see (a) Jaramillo, C.; Knapp, S. Synthesis 1994, 1.
10. (b) Postema, M. H. D. Tetrahedron 1992, 48, 8545.
11. Shono et al. reported that 2-methoxypiperidine derivatives reacted with the silyl enol ether derived from acetophenone under the influence of a stoichiometric amount of titanium tetrachloride. Although an example of the reaction of a 2,3-diacetylpiperidine derivative was shown, the selectivity was not reported. (a) Shono, T.; Matsumura, Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172.
12. (b) Shono, T.; Matsumura, Y.; Onomura, O.; Kanazawa, T.; Habuka, M. Chem. Lett. 1984, 1101.
13. Quite recently, Matsumura et al. reported the reaction of a 2-methoxypiperidine derivative with titanium enolates. Matsumura, Y.; Kanda, Y.; Shirai, K.; Onomura, O.; Maki, T. Org. Lett. 1999, 1, 175.
14. Sugisaki, C. H.; Carroll, P. J.; Correia, C. R. D. Tetrahedron Lett. 1998, 39, 3413.
15. Batey, R. A.; MacKay, D. B.; Santhakumar, V. J. Am. Chem. Soc. 1999, 121, 5075.
16. Prepared from a δ-lactam derivative according to standard procedures.
17. Kobayashi, S. Eur. J. Org. Chem. 1999, 15.
18. Hachiya, I.; Moriwaki, M.; Kobayashi, S. Bull. Chem. Soc. Jpn. 1995, 68, 2053.
19. In our preliminary study, it was revealed that N-BOC-2,3-diacetoxypiperidine was unstable, and that the acetoxy group at the 2-position was easily converted to a hydroxy group. In the early paper of Shono et al., 4b it was reported that N-methoxycarbonyl-2,3-diacetoxypiperidine, which was synthesized using an anodic oxidation method, was readily hydrolized to the 2-hydroxypiperidine derivative. On the other hand, N-Cbz-2,3-diacetoxypiperidine was stable to store even in open air at room temperature.
20. The relative stereochemistry was determined by X-ray analysis.