Photocyclization of 2-azabicyclo[3.3.0]octane-3-carboxylate derivatives: Induced and noninduced diastereoselectivity

Organic Letters

Volumn 3, Issue 4, 2001, Pages 537-539

  Griesbeck, Axel G ^a   Kramer, Wolfgang ^a   Bartoschek, Anna ^a   Schmickler, Hans ^a  

^a Institute of Organic Chemistry   (Germany)

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EID: 0000541886     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006943i     Document Type: Article

References (23)

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8. For example: Wilken, J.; Kossenjans, M.; Saak, W.; Haase, D.; Pohl, S.; Martens, J. Liebigs Ann. 1997, 573.
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10. Kossenjans, M.; Soeberdt, M.; Wallbaum, S.; Harms, K.; Martens, J.; Aurich, H. G. J. Chem. Soc., Perkin Trans. 1 1999, 2353. Wilken, J.; Kossenjans, M.; Saak, W.; Haase, D.; Pohl, S.; Martens, J. Tetrahedron: Asymmetry 1999, 10, 4437. Wilken, J.; Gröger, H.; Kossenjans, M.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2761.
11. Kossenjans, M.; Soeberdt, M.; Wallbaum, S.; Harms, K.; Martens, J.; Aurich, H. G. J. Chem. Soc., Perkin Trans. 1 1999, 2353. Wilken, J.; Kossenjans, M.; Saak, W.; Haase, D.; Pohl, S.; Martens, J. Tetrahedron: Asymmetry 1999, 10, 4437. Wilken, J.; Gröger, H.; Kossenjans, M.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2761.
12. Wilken, J.; Thorey, C.; Gröger, H.; Haase, D.; Saak, W.; Pohl, S.; Muzart, J.; Martens, J. Liebigs Ann. 1997, 2133.
13. The corresponding carbanion gives a 14:86 endo/exo ratio with benzaldehyde: Wilken, J.; Martens, J. Liebigs Ann. 1997, 563.
14. From DCC/DMAP/HOBT-coupling of the benzyl ester of 2-azabicyclo[3.3.0]cctan-3-oic acid with β-alanine and subsequent hydrogenolytic debenzylation (overall yield: 73%).
15. Griesbeck, A. G.; Mauder, H.; Stadtmüller, S. Acc. Chem. Res. 1994, 27, 70. Griesbeck, A. G.; Buhr, S.; Fiege, M.; Lex, J.; Schmickler, H. J. Org. Chem. 1998, 63, 3847.
16. Griesbeck, A. G.; Mauder, H.; Stadtmüller, S. Acc. Chem. Res. 1994, 27, 70. Griesbeck, A. G.; Buhr, S.; Fiege, M.; Lex, J.; Schmickler, H. J. Org. Chem. 1998, 63, 3847.
17. For stereoselective 1,6-photocyclization, see: Griesbeck, A. G.; Heckroth, H.; Schmickler, H. Tetrahedron Lett. 1999, 40, 3137.
18. 3 solution and brine, extraction with AcOEt, and drying, the solvents were evaporated and the residue was purified by column chromatography. B: Photocyclization of 9. A 40 mM solution of 9 in acetone was irradiated for 48 h at rt, filtered over silica, and crystallized from acetone: 96% yield, mp 192-194°C.
19. X-ray structure of 10: Lex, J.; Griesbeck, A. G.; Kramer, W. Z. Kristallogr. 2000, 215, 451.
20. Griesbeck, A. G.; Fiege, M.; Bondock, S.; Gudipati, M. S. Org. Lett. 2000, 2, 3623.
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22. Griesbeck, A. G.; Stadtmüller, S. J. Am. Chem. Soc. 1990, 112, 1281. Griesbeck, A. G.; Stadtmüller, S. J. Am. Chem. Soc. 1991, 113, 6923.
23. Griesbeck, A. G.; Kramer, W.; Oelgemöller, M.; Lex, J. Unpublished results.