An efficient protocol for the oxidative hydrolysis of ketone SAMP hydrazones employing SeO2 and H2O2 under buffered (pH 7) conditions

Synlett

Volumn , Issue 19, 2009, Pages 3131-3134

  Smith III, Amos B ^a   Liu, Zhuqing ^a   Simov, Vladimir ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

Aldol reactions; Ketones; Oxidative cleavage; SAMP; Seo2

Indexed keywords

AMINO 2 METHOXYPYRROLIDINE DERIVATIVE; HYDRAZONE DERIVATIVE; HYDROGEN PEROXIDE; KETONE DERIVATIVE; OXIDE; PYRROLIDINE DERIVATIVE; SELENIUM OXIDE; UNCLASSIFIED DRUG;

ALDOL REACTION; ALKYLATION; ARTICLE; HYDROLYSIS; OXIDATION; PH MEASUREMENT;

EID: 72049107794     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/S-0029-1218352     Document Type: Article

References (13)

1. Enders, D.; Eichenauer, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 549.
2. Job, A.; Janeck, C. F.; Bettray, W.; Peter, R.; Enders, D. Tetrahedron 2002, 58, 2253; and references therein.
3. Enders, D.; Wortmann, L.; Peters, R. Acc. Chem. Res. 2000, 33, 157.
4. Enders, D.; Plant, A. Synlett 1994,1054.
5. Said, S. B.; Skarzewski, J.; Mlochowski, J. Synthesis 1989, 223.
6. Stupp, S. I.; Son, S.; Li, L. S.; Lin, H. C.; Keser, M. J. Am. Chem. Soc. 1995, 117,5212.
7. Eichenauer, H.; Friedrich, E.; Lutz, W.; Enders, D. Angew. Chem., Int. Ed. Engl. 1978, 17, 206.
8. 4 and concentrated. The residue was purified by flash chromatography to provide the desired hydrazone (70-98%).
9. 4, and concentrated. The residue was purified via flash chromatography to provide the corresponding ketone in 68-96% yield.
10. 4, concentrated, and the residue was purified by flash chromatography to furnish the alkylated hydrazone in 90-96% yield.
11. Enders, D.; Bockstiegel, B. Synthesis 1989, 493.
12. 4 and concentrated. The residue was purified by flash chromatography to furnish aldol products in 68-96% yield
13. 2O) to provide β-hydroxy ketones (65-81%).