[2+2]-Photocycloaddition reactions of tetronic acid esters and amides

Synthesis

Volumn , Issue 13, 2010, Pages 2308-2312

  Hehn, Jörg P ^a   Gamba Sánchez, Diego ^a   Kemmler, Michael ^a   Fleck, Martin ^a   Basler, Birte ^a   Bach, Thorsten ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

2+2 cycloadditions; cyclobutanes; diastereoselectivity; heterocycles; photochemistry

Indexed keywords

ACID ESTER; CYCLOADDITIONS; CYCLOBUTANE RING; CYCLOBUTANES; DIASTEREO-SELECTIVITY; DIETHYL ETHERS; HETEROCYCLES; LACTONE RINGS; PHOTOCYCLOADDITION; PHOTOCYCLOADDITION REACTION; REACTION CONDITIONS; RING OPENING; STARTING MATERIALS; TETRACYCLIC PRODUCTS; TETRONIC; TOTAL SYNTHESIS;

ACIDS; AMIDES; BUTANE; ESTERIFICATION; ETHERS; ORGANIC POLYMERS; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

ESTERS;

ALCOHOL; CYCLOBUTANE; ETHER; LACTONE; PROLINE; PUNCTAPORONIN C; SESQUITERPENE DERIVATIVE; TETRONIC ACID AMIDE; TETRONIC ACID DERIVATIVE; TETRONIC ACID ESTER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CYCLOADDITION; IRRADIATION; PHOTOCYCLOADDITION; RING OPENING; SYNTHESIS;

EID: 77953852559     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218793     Document Type: Article

References (38)

1. Hehn J P., Müller C, Bach T, In Handbook of Synthetic Photochemistry Albini A Fagnoni M Wiley-VCH Weinheim 2010 171
2. Hoffmann N, Chem. Rev. 2008 108 1052
3. Iriondo-Alberdi J, Greaney M F., Eur. J. Org. Chem. 2007 4801
4. Fleming S A., In Synthetic Organic Photochemistry (Molecular and Supramolecular Photochemistry) Vol. 12 Griesbeck, A. G.; Mattay, J., Eds.; New York 2005 141
5. Margaretha P, In Synthetic Organic Photochemistry (Molecular and Supramolecular Photochemistry) Vol. 12 Griesbeck, A. G.; Mattay, J., Eds.; Dekker New York 2005 211
6. Pete J P., In CRC Handbook of Organic Photochemistry and Photobiology 2nd ed. W. M.; Lenci, F., Eds CRC Press Boca Raton 2004 71-1
7. Bach T, Synthesis 1998 683
8. Fleming S A., Bradford C L., Gao J J., In Organic Photochemistry (Molecular and Supramolecular Photochemistry) Vol. 1 Ramamurthy, V.; Schanze, K. S., Eds.; Dekker New York 1997 187
9. Pete J.-P, In Advances in Photochemistry Vol. 21 Neckers, D. C.;Volman, D. H.; v. Bnau, G., Eds. Wiley New York 1996 135
10. Mattay J, Conrads R, Hoffmann R, In Methoden der Organischen Chemie (Houben-Weyl) 4th ed., Vol. [nl]E 21c Helmchen G Hoffmann R W. Mulzer J Schaumann E, Eds. Thieme Stuttgart 1995 3085
11. Crimmins M T., Reinhold T L., Org. React. 1993 44 297
12. Crimmins M T., Chem. Rev. 1988 88 1453
13. Baldwin S W., Org. Photochem. 1981 5 123
14. Bauslaugh P G., Synthesis 1970 287
15. Kemmler M, Bach T, Angew. Chem. Int. Ed. 2003 42 4824
16. Angew. Chem. 2003, 115, 4973
17. Kemmler M, Herdtweck E, Bach T, Eur. J. Org. Chem. 2004 4582
18. Fleck M, Bach T, Angew. Chem. Int. Ed. 2008 47 6189
19. Angew. Chem. 2008, 120, 6284
20. Seebach D, Matthews J L., J. Chem. Soc., Chem. Commun. 1997 2015
21. Cheng R P., Gellman S H., DeGrado W F., Chem. Rev. 2001 101 3219
22. Basler B, Schuster O, Bach T, J. Org. Chem. 2005 70 9798
23. Curtius F W., Scharf H.-D, Tetrahedron: Asymmetry 1996 7 2957
24. Schuster D I., In CRC Handbook of Organic Photochemistry and Photobiology 2nd ed. Horspool W M. Lenci F, Eds. CRC Press Boca Raton 2004 72-1
25. Schuster D I., Lem G N., Kaprinidis A, Chem. Rev. 1993 93 3
26. Srinivasan R, HillCarlough K, J. Am. Chem. Soc. 1967 89 4932
27. Liu R S. H., Hammond G S., J. Am. Chem. Soc. 1967 89 4936
28. Vogt F, Jödicke K, Schröder J, Bach T, Synthesis 2009 4268
29. Hehn J P., Kemmler M, Bach T, Synlett 2009 1281
30. Fleck M, Yang C, Wada T, Inoue Y, Bach T, Chem. Commun. 2007 822
31. Anderson J R., Edwards R L., Poyser J P., Whalley A J. S., J. Chem. Soc., Perkin Trans. 1 1988 823
32. Anderson J R., Edwards R L., Freer A A., Mabelis R P., Poyser J P., Spencer H, Whalley A J. S., J. Chem. Soc., Chem. Commun. 1984 917
33. Anderson J R., Briant C E., Edwards R L., Mabelis R P., Poyser J P., Spencer H, Whalley A J. S., Freer A A., J. Chem. Soc., Chem. Commun. 1986 984
34. Sato T, Yoshimatsu K, Otera J, Synlett 1995 843
35. Bajwa J S., Anderson R C., Tetrahedron Lett. 1990 31 6973
36. Farina F, Martín M V., Sánchez F, Maestro M C., Martín M R., Synthesis 1983 397
37. Martín M R., Mateo A I., Tetrahedron: Asymmetry 1994 5 1385
38. Chen Q, Geng Z, Huang B, Tetrahedron: Asymmetry 1995 6 401