Unexpected ring transformations on functionalization of 2-(ω-alken-1-yl)-3,3,3-trifluoroalanine derivatives

Monatshefte fur Chemie

Volumn 134, Issue 1, 2003, Pages 69-80

  Burger, Klaus ^a   Mütze, Kerstin ^a   Osipov, Sergej N ^b   Tsouker, Pavel ^a   Schier, Annette ^c  

^a UNIVERSITY OF LEIPZIG   (Germany)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^c TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

2 ( Alken 1 yl) 3,3,3 trifluoroalanine; 3,3 Dimethyl 2 trifluoromethyl 4 hydroxyproline; 3a Methoxy 6a trifluoromethyl tetrahydrofurano 2,3d oxazoline; 4 Trifluoromethyl 5,6 dihydro 4H 1,3 oxazines; Epoxidation; NBS Bromination

Indexed keywords

EID: 0037221897     PISSN: 00269247     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00706-002-0521-8     Document Type: Article

References (24)

1. (a) Koksch B, Sewald N, Jakubke H-D, Burger K (1996) Biochemical frontiers of fluorine chemistry. In: Ojima I, McCarthy JR, Welch JT (eds) ACS Symposium Series No. 639, American Chemical Society, Washington DC, p 42;
2. Sewald N, Burger K (1995) Synthesis of β-Fluorine-containing Amino Acids. In: Kukhar' VP, Solshonok VA (eds) Fluorine-containing Amino Acids: Synthesis and Properties, John Wiley & Sons, Chichester, p 139
3. Kukhar' VP (1995) J Fluorine Chem 69: 199
4. (a) For a review see: Gerig JT (1978) In: Berliner LS, Reuben J (eds) Biological Magnetic Resonance Vol. 1, Plenum Press, New York p 139;
5. (b) Gerig JT (1989) Methods Enzymol 3: 177;
6. (c) Gregory DH, Gerig JT (1991) Biopolymers 31: 845;
7. (d) Cushmann M, Patel HH, Scheuring J, Bacher A (1992) J Org Chem 57: 5630
8. Kollonitsch J (1982) In: Filler R, Kobayashi Y (eds) Biomedicinal Aspects of Fluorine Chemistry, Kodansha, Tokyo and Elsevier Biomedical Press, Amsterdam p 93, and references cited therein
9. Burger K, Gaa K, Mütze K (1991) Chem Ztg 115: 328
10. Soloshonok VA, Gerus II, Yagupol'skii YuL (1987) Zh Org Khim 28: 2308
11. Burger K, Gaa K (1990) Chem Ztg 114: 101
12. Baldwin JE (1976) JCS Chem Commun 734, and (1976) JCS Chem Commun 736
13. Baldwin JE (1976) JCS Chem Commun 734, and (1976) JCS Chem Commun 736
14. (a) Burger K, Huber E, Schöntag N, Ottlinger R (1983) JCS Chem Commun 945;
15. (b) Sewald N, Burger K (1989) J Fluorine Chem 45: 84;
16. (c) Osipov SN, Kolomiets AF, Fokin AV (1990) Izv Akad Nauk SSSR, Ser Khim 2456; (1990) Bull Acad Sci USSR, Chem Sec 2228;
17. (c) Osipov SN, Kolomiets AF, Fokin AV (1990) Izv Akad Nauk SSSR, Ser Khim 2456; (1990) Bull Acad Sci USSR, Chem Sec 2228;
18. (d) Osipov SN, Kolomiets AF, Fokin AV (1989) J Fluorine Chem 45: 159
19. 2/3; a = 0.0561, b = 0.33. Anisotropic thermal parameters and complete lists of interatomic distances and angles have been deposited with the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK. The data are available on request on quoting CCDC-186573
20. (a) Seebach D, Renaud P, Schweizer WB, Züger MF (1984) Helv Chim Acta 67: 1843;
21. (b) Wucherpfennig U (1992) PhD Thesis, Technical University Munich
22. Ohfune Y, Hori K, Sakaitani M (1986) Tetrahedron Lett 27: 6079
23. Gaa K (1990) PhD Thesis, Technical University Munich
24. Kalinowski H-O, Berger S, Braun S (1984) (13)C-NMR-Spektroskopie, G. Thieme Verlag, Stuttgart, p 168