4-Penteneselenothioic acid S-alkyl esters: Synthesis via the seleno-Claisen rearrangement

Tetrahedron

Volumn 53, Issue 36, 1997, Pages 12237-12247

  Murai, Toshiaki ^a   Takada, Hiroya ^a   Kakami, Kaori ^a   Fujii, Makiko ^a   Maeda, Masahiko ^a   Kato, Shinzi ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOSELENIUM DERIVATIVE; ORGANOSULFUR DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030880668     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00556-5     Document Type: Article

References (35)

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14. 10 and seleno-Claisen rearrangement is not easy, the latter one proceeds as smoothly as the former one even if a selenocarbonyl group, which has been believed to be an unstable functional group, is formed in the latter case.
15. (a) Metzner, P. Phosphorus, Sulfur, and Silicon, 1991, 59, 1.
16. (b) Metzner, P. Synthesis 1992, 1185.
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19. Wipf, P. in Comprehensive Organic Syntheses; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p. 827.
20. In the latter step, 2-butenyl group can approach to a vinyl group (Equation Presented) from the side close to either methyl group or vinyl group if 20 adopts an eclipse comformation through the bond depicted with bold line as shown right.
21. 14 The stereochemistry of 22 was further confirmed by a phase sensitive NOESY spectrum.
22. Kagan, H. B. Ed., Stereochemistry, Georg Thieme Publishers; Stuttgart: 1977; Vol. 1-2, p. 63.
23. On the basis of a phase sensitive NOESY spectrum the product 23 was tentatively assigned to be a threo isomer.
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25. Murai, T.; Kakami, K.; Kanda, T.; Kato, S. Tetrahedron, 1996, 52, 2839.
26. Ester 26 was obtained as a stereoisomeric mixture in a ratio of 92 : 8, although the stereochemistry has not been determined.
27. Protodesilylation of 26 with KF in MeOH proceeded smoothly to give ester 18.
28. The protodesilylation was complete mainly during the purification of the products by column chromatography on silica gel. In some cases the silyl group was partly replaced with proton in the aqueous work-up.
29. (a) Kato, S.; Murai, T.; Ishida, M. Org. Prep. Proceds. Int., 1986, 18, 369.
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