Dithiane- and trithiane-based photolabile scaffolds for molecular recognition

Organic Letters

Volumn 3, Issue 12, 2001, Pages 1841-1843

  Mitkin, Oleg D ^a   Kurchan, Alexei N ^a   Wan, Yongqin ^a   Schiwal, Brian F ^a   Kutateladze, Andrei G ^a  

^a UNIVERSITY OF DENVER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND;

ARTICLE; CHEMISTRY; PHOTOCHEMISTRY;

HETEROCYCLIC COMPOUNDS; PHOTOCHEMISTRY;

EID: 0035859334     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015933u     Document Type: Article

References (24)

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11. (b) Mitkin, O. D.; Wan, Y.; Kurchan, A. N.; Kutateladze, A. G. Synthesis 2001, in press.
12. 3) δ (ppm) 7.42-7.22 (5H, m), 4.25 (1H. d, J = 6.6 Hz), 4.22 (1H, d, J = 6.6 Hz), 2.92-2.73 (4H, m), 2.12-2.04 (1H, m), 1.82-1.92 (1H, m).
13. Gyenes, F.; Bergmann, K. E.; Welch, J. T. J. Org. Chem. 1998, 63, 2824.
14. More experimental details can be found in the Supporting Information.
15. Downfield shift of N-H protons is indicative of H-bonding; see, for example: (a) Ösapay, K.; Case, D. A. J. Am. Chem. Soc. 1991, 113, 9436.
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18. 4). Direct irradiation of 4b in acetonitrile produced only the corresponding imine and products of its hydrolysis. After chromatographic separation, 17% of the imine, Ar′CH= N-Py, was isolated along with 35% of the aldehyde, Ar′CHO, 39% of 2-amino-5-nitropyridine and 21% of unreacted 4b, accounting for at least 71% in C-C bond cleavage.
19. (a) Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1996, 118, 7128.
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23. (a) p-Ethoxyethoxybenzaldehyde was used for improved solubility in organic solvents.
24. (b) We did not separate individual diastereomers of 11 (2:1 ratio by NMR). 2,4-Disubstituted trithianes, formed by electrophilic quenching of lithiated trithianes, are believed to have cis geometry (see Fukunaga, M.; Sugawara, T.; Oki, M. Chem. Lett. 1972, 1, 55). and we therefore assume that the observed diastereomers are the meso and d,l pair as a result of the two chiral benzylic centers generated as a result of the anion addition to imine, not the cis-trans isomers.