RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2005(13): 2137-2142
DOI: 10.1055/s-2005-869967
DOI: 10.1055/s-2005-869967
PAPER
© Georg Thieme Verlag Stuttgart · New York
Efficient Synthesis of N-Protected Trisubstituted Oxazolidines from Ketones, Vinyl Ethers, and Fluoroalkanesulfonyl Azides in Mild Conditions
Weitere Informationen
Received
27 January 2005
Publikationsdatum:
20. Juni 2005 (online)
Publikationsverlauf
Publikationsdatum:
20. Juni 2005 (online)
![](https://www.thieme-connect.de/media/synthesis/200513/lookinside/thumbnails/10.1055-s-2005-869967-1.jpg)
Abstract
A facile one-step method has been developed for the synthesis of 2,3,5-trisubstituted oxazolidines in moderate yields by the three-component reaction of ketones, vinyl ethers, and fluoroalkanesulfonyl azides at 0 °C within five minutes. This practical synthetic method provides a convenient and expeditious access to N-per(poly)fluoroalkanesulfonyl oxazolidines.
Key words
fluoroalkanesulfonyl azide - ketone - vinyl ether - oxazolidine - multi-component reactions
- 1
Anastasm PT.Warner JC. Green Chemistry: Theory and Practice Oxford University Press; Oxford: 1998. - 2
Domling A.Ugi I. Angew. Chem. Int. Ed. 2000, 39: 3168 -
3a
Okuyama Y.Nakano H.Hongo H. Tetrahedron: Asymmetry 2000, 11: 1193 -
3b
Falorni M.Collu C.Conti S.Giacomelli G. Tetrahedron: Asymmetry 1996, 7: 293 -
3c
Joshi NN.Prasad PRK. J. Org. Chem. 1997, 62: 3770 -
4a
Wagner B.Gonzalez GI.Tran Hun Dau ME.Zhu J. Bioorg. Med. Chem. 1999, 7: 737 -
4b
Guerrier L.Royer J.Grierson DS.Husson HP. J. Am. Chem. Soc. 1983, 105: 7754 -
5a
Semenov VP. Khim. Geterotsikl. Soedin. 1976, 12: 1613 -
5b
Semenov VP.Stroiman IM.Ogloblin KA. Khim. Geterotsikl. Soedin 1977, 1: 27 -
5c
Semenov VP.Stroiman IM.Ozemaya SV.Ogloblin KA. Khim. Geterotsikl. Soedin. 1977, 3: 332 -
6a
Ramachandran PV. In Asymmetric Fluoroorganic Chemistry: Synthesis, Applications and Future Directions, ACS Symposium Series 746 American Chemical Society; Washington DC: 2000. -
6b
Ojima I.McCarthy JR.Welch JT. In Biomedical Frontiers of Fluorine Chemistry, ACS Symposium Series 639 American Chemical Society; Washington DC: 1996. -
6c
Kukhar’ VP.Soloshonok VA. In Fluorine-containing Amino Acids: Synthesis and Properties Wiley; New York: 1995. -
6d
Welch JT. In Selective Fluorination in Organic and Bioorganic Chemistry, ACS Symposium Series 456 American Chemical Society; Washington DC: 1991. -
6e
Welth JT.Eswarakrishnan S. In Fluorine in Bioorganic Chemistry Wiley-Interscience John Wiley & Sons; New York: 1991. -
7a
Young JA.Simmons TC.Hoffmann FN. J. Am. Chem. Soc. 1956, 78: 5637 -
7b
Middleton WJ.Krespan CG. J. Org. Chem. 1967, 32: 951 -
7c
O’Brien BA.Lam WY.DesMarteau DD. J. Org. Chem. 1986, 51: 4466 - 8
Gosselin F.Roy A.O’Shea PD.Chen CY.Volante RP. Org. Lett. 2004, 6: 641 -
9a
Xu Y.Wang YL.Zhu SZ. J. Fluorine Chem. 2000, 104: 195 -
9b
Xu Y.Zhu SZ. Tetrahedron 2001, 57: 669 -
9c
Zhu SZ.Jin GF.Zhao JW. J. Fluorine Chem. 2003, 120: 65 - 10
Zhu SZ.He P.Zhao JW.Cai X. J. Fluorine Chem. 2004, 125: 445 - 11
Weuthen M.Scharf HD.Runsink J. Chem. Ber. 1987, 120: 1023 - 14
Wang LJ.Seiders JR.Floreancig PE. J. Am. Chem. Soc. 2004, 126: 12596 - 15
Zhu SZ. Tetrahedron Lett. 1992, 33: 6503
References
He, P.; Zhu, S. Z. Tetrahedron 2005, in press.
13CCDC number: CCDC 262795