The reaction of singlet oxygen with enecarbamates: A mechanistic playground for investigating chemoselectivity, stereoselectivity, and vibratioselectivity of photooxidations

Accounts of Chemical Research

Volumn 41, Issue 3, 2008, Pages 387-400

  Sivaguru, J ^a   Solomon, Marissa R ^b   Poon, Thomas ^c   Jockusch, Steffen ^b   Bosio, Sara G ^d   Adam, Waldemar ^d,e   Turro, Nicholas J ^b  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

^b Och Spine at New York Presbyterian Hospitals   (United States)

^c KECK GRADUATE INSTITUTE   (United States)

^d UNIVERSITY OF WÜRZBURG   (Germany)

^e UNIVERSITY OF PUERTO RICO   (Puerto Rico)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BENZOIN; CARBAMIC ACID DERIVATIVE; DRUG DERIVATIVE; SINGLET OXYGEN;

CHEMISTRY; OXIDATION REDUCTION REACTION; PHOTOCHEMICAL SMOG; PHOTOCHEMISTRY; REVIEW; STEREOISOMERISM; SYNTHESIS;

ALKENES; BENZOIN; CARBAMATES; OXIDANTS, PHOTOCHEMICAL; OXIDATION-REDUCTION; PHOTOCHEMISTRY; SINGLET OXYGEN; STEREOISOMERISM;

EID: 42449132925     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar7001254     Document Type: Review

References (24)

1. Chiral Photochemistry, Inoue, Y., Ramamurthy, V.; Eds.; Marcel Dekker: New York, 2004.
2. Inoue, Y. Asymmetric photochemical reactions in solution. Chem. Rev. 1992, 92, 741-770.
3. Rau, H. Asymmetric photochemistry in solution. Chem. Rev. 1983, 83, 535-547.
4. Turro, N. J. Supramolecular organic photochemistry: control of covalent bond formation through noncovalent supramolecular interactions and magnetic effects. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4805-4809.
5. Singlet Oxygen, Wasserman, H. H., Murray, R. W.; Eds.; Academic Press: New York; 1979.
6. Singlet Oxygen, Frimer, A. A.; Ed.; CRC Press: Boca Raton, FL, 1985; Vols. 1-4.
7. Foote, C. S. Photosensitized oxygenations and the role of singlet oxygen. Acc. Chem. Res. 1968, 1, 104-110.
8. Adam, W.; Bosio, S. G.; Turro, N. J.; Wolff, B. T. Enecarbamates as selective substrates in oxidations: Chiral-auxiliary-controlled mode selectivity and diastereoselectivity in the [2 + 2] cycloaddition and ene reaction of singlet oxygen and in the epoxidation by DMD and mCPBA. J. Org. Chem. 2004, 69, 1704-1715.
9. Sivaguru, J.; Poon, T.; Franz, R.; Jockusch, S.; Adam, W.; Turro, N. J. Stereocontrol within confined spaces: Enantioselective photooxidation of enecarbamates inside zeolite supercages. J. Am. Chem. Soc. 2004, 126, 10816-10817.
10. Sivaguru, J.; Saito, H.; Solomon, M. R.; Kaanumalle, L. S.; Poon, T.; Jockusch, S.; Adam, W.; Ramamurthy, V.; Inoue, Y.; Turro, N. J. Control of chirality by cations in confined spaces: Photooxidation of enecarbamates inside zeolite supercages. Photochem. Photobiol. 2006, 82, 123-131.
11. Poon, T.; Sivaguru, J.; Franz, R.; Jockusch, S.; Martinez, C.; Washington, I.; Adam, W.; Inoue, Y.; Turro, N. J. Temperature and solvent control of the stereoselectivity in the reactions of singlet oxygen with oxazolidinone-substituted enecarbamates. J. Am. Chem. Soc. 2004, 126, 10498-10499.
12. Sivaguru, J.; Poon, T.; Hooper, C.; Saito, H.; Solomon, M.; Jockusch, S.; Adam, W.; Inoue, Y.; Turro, N. J. A comparative mechanistic analysis of the stereoselectivity trends observed in the oxidation of chiral oxazolidinone-functionalized enecarbamates by singlet oxygen, ozone and triazolinedione. Tetrahedron 2006, 62, 10647-10659.
13. Sivaguru, J.; Solomon, M. R.; Saito, H.; Poon, T.; Jockusch, S.; Adam, W.; Inoue, Y.; Turro, N. J. Conformationally controlled (entropy effects), stereoselective vibrational quenching of singlet oxygen in the oxidative cleavage of oxazolidinone-functionalized enecarbamates through solvent and temperature variations. Tetrahedron 2006, 62, 6707-6717.
14. Prein, M.; Adam, W. The Schenck ene reaction: Diastereoselective oxyfunctionalization with singlet oxygen in synthetic applications. Angew. Chem., Int. Ed. Engl. 1996, 35, 471-494.
15. Kagan, H. B.; Fiaud, J. C. Kinetic resolution. Top. Stereochem. 1988, 18, 249-330.
16. Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Practical considerations in kinetic resolution reactions. Adv. Synth. Catal. 2001, 343, 5-26.
17. Leffler, J., E. The enthalphy-entropy relationship and its implications for organic chemistry. J. Org. Chem. 1955, 20, 1202-1231.
18. Leffler, J., E. The interpretation of enthalpy and entropy data. J. Org. Chem. 1966, 31, 533-537.
19. Buschmann, H.; Scharf, H.-D.; Hoffmann, N.; Esser, P. The isoinversion principle - a general model of chemical selectivity. Angew. Chem., Int. Ed. Engl. 1991, 30, 477-515.
20. Refer Supporting Information for details.
21. Sivaguru, J.; Saito, H.; Poon, T.; Omonuwa, T.; Franz, R.; Jockusch, S.; Hooper, C.; Inoue, Y.; Adam, W.; Turro, N. J. Stereoselective photooxidation of enecarbamates: Reactivity of ozone vs singlet oxygen. Org. Lett. 2005, 7, 2089-2092.
22. Turro, N. J. The role of intersystem crossing steps in singlet oxygen chemistry and photo-oxidations. Tetrahedron 1985, 41, 2089-2098.
23. Evans, D. A.; Chapman, K. T.; Hung, D. T.; Kawaguchi, A. T. Transition state π-solvation by aromatic rings: An electronic contribution to Diels-Alder reaction diastereoselectivity. Angew. Chem., Int. Ed. Engl. 1987, 26, 1184-1186.
24. Poon, T.; Turro, N. J.; Chapman, J.; Lakshminarasimhan, P.; Lei, X.; Jockusch, S.; Franz, R.; Washington, I.; Adam, W.; Bosio, S. G. Stereochemical features of the physical and chemical interactions of singlet oxygen with enecarbamates. Org. Lett. 2003, 5, 4951-4953.