Unexpected formation of O-methoxycarbonyl cyanohydrin showing potential as a protective group of ketones

Synlett

Volumn , Issue 9, 1999, Pages 1423-1425

  Poirier, Donald ^a   Berthiaume, David ^a   Boivin, Roch P ^a  

^a UNIVERSITÉ LAVAL   (Canada)

Author keywords

Carbonate; Cyanohydrin; Ketone; Protective group

Indexed keywords

ACID; ALIPHATIC AMINE; CARBONYL DERIVATIVE; FORMIC ACID DERIVATIVE; KETONE; NITRILE;

ARTICLE; CHEMOREACTIVITY; REACTION ANALYSIS; SYNTHESIS;

EID: 0032849309     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2859     Document Type: Article

References (15)

1. Greene, T. W.; Wuts, P. G. M. In Protective groups in organic synthesis, 2nd ed.; Wiley-Interscience: New York, 1991; pp 175-223.
2. Klimstra, P. D.; Colton, F. B. Steroids 1967, 10, 411.
3. Hiyama, T.; Oishi, H.; Saimoto, H. Tetrahedron Lett. 1985, 26, 2459.
4. Evans, D. A.; Hoffman, J. M.; Truesdale, L. K. J. Am. Chem. Soc. 1973, 95, 5822.
5. Evans, D. A.; Wong, R. Y. J. Org. Chem. 1977, 42, 350.
6. Duboudin, F.; Cazeau, Ph.; Moulines, F.; Laporte, O. Synthesis 1982, 212.
7. Rawal, V. H.; Rao, J. A.; Cava, M. P. Tetrahedron Lett. 1985, 26, 4275.
8. Stork, G.; Maldonado, L. J. Am. Chem. Soc. 1971, 93, 5286.
9. deRuggieri, P.; Ferrari, C. J. Am. Chem. Soc. 1959, 81, 5725.
10. Tremblay, M. R.; Poirier, D. J. Steroid Biochem. Molec. Biol. 1998, 66, 179.
11. Tremblay, M. R.; Auger, S.; Poirier, D. Synth. Commun. 1995, 25, 2483.
12. Sam, K. M.; Boivin, R. P.; Tremblay, S.; Auger, S.; Poirier, D. Drug Design Discovery 1998, 15, 157.
13. 1H NMR without (Table 1) or with (Table 2) a purification by silica gel column chromatography.
14. +.
15. 2O (3:1) (10 mL) was added to a solution of O-methoxycarbonyl cyanohydrin 2 (0.27 mmol) in McOH (10 mL). After 4 h at room temperature, water was added, and 3-methyl-O-estrone (one spot on TLC) was extracted with EtOAc. Poirier, D.; Labrie, C; Mérand, Y.; Labrie, F. J. Steroid Biochem. Molec. Biol.s 1991, 38, 759.